Nucleobases Adenine Research Articles

Thermochemical and Structural Analysis of Tautomers of Sulfur and Selenium Modified RNA Nucleobases

Nucleobases (adenine, cytosine, guanine, and uracil), the four molecules that forms RNA, have been found to be useful in probing in the human body when modified because they can emit light. Non-modified nucleobases do not exhibit emissive properties and cannot be used as probes. Some of the modifications include the substitution of nitrogen atoms with sulfur and selenium, and the resulting modified nucleobases give place to the so-called tz- and ts- RNA alphabets, respectively. Therefore, the aim of this project was to provide insights about the viability, from a computational perspective, of using the modified nucleobases as probes, evaluating the differences in thermochemical, structural and emissive properties of the modified nucleobases with respect to the non-modified ones. Nucleobases can coexist with other modified nucleobases or tautomers, molecules that differ due to the change in position of hydrogen atoms in a molecule’s structure and as a result have different physical and chemical properties. The thermochemical properties evaluation mainly consisted in the computation of the relative Gibbs Free Energy (G), which is related to the fraction F, an index of the relative population among tautomers. This was done using Gaussian 09 software by performing geometry analysis and frequency computations on each one of the tautomers. By comparing the equilibrium fractions, it was determined that in both cases, tz- and ts- guanine and cytosine exist principally in the form of one of their tautomers (Cytosine 2 and Guanine 2) as in the case of the non-modified cases. After confirming which tz- and ts- tautomers were the ones with the largest probable population, infrared (IR) and ultraviolet-visible (UV-vis) spectra were obtained. The IR spectra of selenium and sulfur tautomers of guanine and cytosine indicated that the tautomers had peaks at similar frequencies with respect to each other, however, the intensities varied, implying slight structural changes between the tautomers. On the other hand, the UV-vis spectra showed a change in peak positions between the tautomers with sulfur and selenium, suggesting that the change between sulfur and selenium has an effect on the spectra by shifting the peaks from the original molecules’ λmax values. Their relative population fractions show that only the canonical forms of the modified nucleobases exist in a larger extent than the rest of their tautomer forms. In addition, the features in their UV-vis and IR spectra allow these tautomers to be differentiated from each other.

Bio-adenine-bridged molecular design approach toward non-covalent functionalized graphene by liquid-phase exfoliation

Here, the supramolecular interaction between nucleobase adenine and graphene was strengthened by a novel chemical molecular designing strategy. Based on this approach, the adenine-bridged aromatic phthalonitrile (AAPN) was prepared as stabilizer toward liquid-phase exfoliation for non-covalent functionalized graphene (AAPN-G). A series of experiments were carried out to verify the strong supramolecular interaction between AAPN and graphene. The feasibility of multifunctional application of the AAPN was briefly demonstrated. This work constitutes a feasible strategy in the preparation and functionalization of graphene that could be extended to some other (bio)molecules toward realization of designing multifunctional materials.

Individual Identification of DNA Nucleobases on Atomically Thin Black Phosphorene Nanoribbons: van der Waals Corrected Density Functional Theory Calculations

Monolayer-based nanodevices hold great promise for the next-generation sequencing (biomolecular sensing/DNA sequencing)-based applications. In this study, we have investigated the interaction of the four nucleobases (adenine, guanine, thymine, and cytosine) on a phosphorene nanoribbon-based device armchair phosphorene nanoribbon (APNR) for individual identification of DNA nucleobases. Using the van der Waals corrected (PBE + vdW) density functional theory calculations, we have computed and analyzed the effect of interaction on the transmission properties of the APNR-based nanodevice. The change in the electronic transport properties of APNR when nucleobases are physisorbed has been investigated by using the nonequilibrium Green’s function calculations. The coupling strength is different to some extent for different nucleobases, resulting in different transmission dips due to Fano resonance.

Gas-Phase Reactions of Deprotonated Nucleobases with H, N, and O Atoms.

Complex organic molecules, the hallmark of terrestrial life, are increasingly detected in exotic environments throughout the universe. Our studies probe the ion chemistry of these biomolecules. We report gas-phase reaction rate constants for five deprotonated nucleobases (adenine, cytosine, guanine, thymine, and uracil) reacting with the atomic species H, N, and O. Hydrogen atoms react at moderate rates via associative electron detachment. Oxygen atom reactions occur more rapidly, generating complex product distributions; reaction pathways include associative electron detachment, substitution of the hydrogen atom by an oxygen atom, and generation of OCN-. Nitrogen atoms do not react with the nucleobase anions. The reaction thermodynamics were investigated computationally, and reported product channels are exothermic. Many of the proposed products have been observed in various astrochemical environments. These reactions provide insight into chemical processes that may occur at the boundaries between diffuse and dense interstellar clouds and in complex extraterrestrial ionospheres.

Functionalization of zigzag graphene nanoribbon with DNA nucleobases-A DFT study

The density functional theory (DFT) calculations on the chemical functionalization of zigzag graphene nanoribbon (ZGNR) with DNA (Deoxyribonucleic acid) nucleobases were carried out using the local density approximation (DFT-LDA). The binding energies, charge transfer, equilibrium geometries and band gap variations of bare ZGNR (b-ZGNR) and nucleobase functionalized ZGNR (nb-ZGNR), were examined at an electron temperature of 300 K. The functionalization of ZGNR with nucleobases adenine (Anb-ZGNR) and cytosine (Cnb-ZGNR) reveals a significant structural deformation compared to bare ZGNR(b-ZGNR).Our findings suggest that functionalization at the edge of ZGNR is effective in tuning its electronic and structural properties through significant enhancement of dipole moment, reduction in %s character and structural asymmetry, thereby suggesting the possibilities of using functionalized ZGNR as nanocarriers in biomedical applications.

Antenna-like Ring Structures via Self-Assembly of Octaphosphonate Tetraphenyl Porphyrin with Nucleobases.

Supramolecular self-assembly of an octaphosphonate tetraphenyl porphyrin with three different nucleobases (adenine, cytosine, and thymine) was studied. Porphyrin 1 with 8 and 10 equiv of cytosine produces light-harvesting ring-like structures, that is, architectures similar to those observed in natural light-harvesting antenna. However, porphyrin assembled with adenine or thymine resulted in prisms and microrods, respectively. UV–vis absorption, fluorescence, and dynamic light scattering were used to determine the mode of aggregation in solution. Scanning electron microscopy and X-ray diffraction spectroscopy used to visualize the self-assembled nanostructures and their behavior in the solid state, respectively. Thus, we believe that this study may demonstrate a deeper understanding on how one needs to manipulate donor/acceptor subunits in supramolecular assemblies to construct artificial antenna architectures.

Application of TMAH thermochemolysis to the detection of nucleobases: Application to the MOMA and SAM space experiment

Thermochemolysis of seven nucleobases—adenine, thymine, uracil, cytosine, guanine, xanthine, and hypoxanthine—in tetramethylammonium hydroxide (TMAH) was studied individually by pyrolysis gas chromatography mass spectrometry in the frame of the Mars surface exploration. The analyses were performed under conditions relevant to the Sample Analysis at Mars (SAM) instrument of the Mars Curiosity Rover and the Mars Organic Molecule Analyzer (MOMA) instrument of the ExoMars Rover. The thermochemolysis products of each nucleobase were identified and the reaction mechanisms studied. The thermochemolysis temperature was optimized and the limit of detection and quantification of each nucleobase were also investigated. Results indicate that 600°C is the optimal thermochemolysis temperature for all seven nucleobases. The methylated products trimethyl-adenine, 1, 3-dimethyl-thymine, 1, 3-dimethyl-uracil, trimethyl-cytosine, 1, 3, 7-trimethyl-xanthine (caffeine), and dimethyl-hypoxanthine, respectively, are the most stable forms of adenine, thymine, uracil, cytosine, guanine, and xanthine, and hypoxanthine in TMAH solutions. The limits of detection for adenine, thymine, and uracil were 0.075 nmol; the limits of detection for guanine, cytosine, and hypoxanthine were higher, at 0.40, 0.55, and 0.75 nmol, respectively. These experiments allowed to well constrain the analytical capabilities of the thermochemolysis experiments that will be performed on Mars to detect nucleobases.

Entrapment of an adenine derivative by a photo-irradiated uracil-functionalized micelle confers controlled self-assembly behavior

HypothesisInvoking cooperative assembly of the uracil-functionalized supramolecular polymer BU-PPG [uracil end-capped poly(propylene glycol)] upon association with the nucleobase adenine derivative A-MA [methyl 3-(6-amino-9H-purin-9-yl)propanoate] as a model drug provides a new concept to control and tune the properties of supramolecular complexes and holds significant potential for the development of safer, more effective drug delivery systems. ExperimentsBU-PPG and A-MA were successfully developed and exhibited specific recognition and high affinity, which enabled reversible complementary adenine-uracil (A-U) hydrogen bonding-induced formation of spherical micelles in aqueous solution. The self-assembly and controllable A-MA release behavior of BU-PPG/A-MA micelles were studied using morphological analysis and optical and light scattering techniques to investigate the effect of photoirradiation and temperature on the complementary hydrogen bond interactions between BU-PPG and A-MA. FindingsThe resulting micelles possess unusual physical properties, including controlled photoreactivity kinetics, controllable self-assembled morphology and low cytotoxicity in vitro, as well as reversible temperature-responsive behavior. Importantly, irradiated micelles exhibited excellent long-term structural stability under normal physiological conditions and serum disturbance. Increasing the temperature triggered rapid release of A-MA by disrupting A-U complexes. These findings represent an entirely new, promising strategy for the development of multi-controlled release drug delivery nanocarriers based on complementary hydrogen bonding interactions.

Nucleobase sensing using highly-sensitive surface-enhanced Raman spectroscopy templates comprising organic semiconductor peptide nanotubes and metal nanoparticles

Templates formed from aligned diphenylalanine nanotubes with plasmon-active metal nanoparticles are a promising nanocomposite for large-scale, rapid, stable, and cost-effective surface-enhanced Raman spectroscopy (SERS) substrates. The high sensitivity of such templates arises from an arrangement of densely packed plasmon-active silver nanoparticles that enhance the localized electromagnetic field and allow the detection of the nucleobases adenine, cytosine, thymine, uracil, and guanine at concentrations in the range 10−5 to 10−9 M. Blinking of the SERS signal is observed, indicating sensitivity down to the single or few molecule limit. Such blinking could result from charge transfer processes. These results demonstrate the potential for using aligned diphenylalanine nanotube-metal nanoparticle templates for practical monitoring of biomolecules and are promising initial steps toward the use of peptide nanotube-based templates in diagnostic sensing applications.

Hydrogen-Atom Addition to Nucleobases in the Solid State: Characterization of the Corresponding Muoniated Radicals Using μSR.

The radicals formed by muonium (Mu) addition to four nucleobases (adenine, guanine, cytosine, and thymine) have been characterized by avoided level-crossing muon spin resonance (ALC-μSR). Mu is considered to be a light isotope of the hydrogen atom, and the muoniated radicals observed by ALC-μSR are isotopomers of the radicals initially produced by H addition to the nucleobases. The observed radicals have been assigned by considering the relative energies of the possible radicals reported in the literature and comparing the experimental muon and proton hyperfine coupling constants with values from previously reported electron paramagnetic resonance and ab initio calculations that have been scaled to account for the larger magnetic moment of the muon and its lighter mass compared with the proton. Mu addition is observed to occur only at secondary carbons of the purine rings in adenine and guanine. Mu adds to C8 and C2 of adenine with the relative amount being ∼70:30%, and Mu adds exclusively to C8 of guanine. Mu addition is predominantly to the secondary carbons of the pyrimidine ring in cytosine (C5 and C6 with relative yields ∼80:20%) with a small amount of addition at N3. Mu adds to both the secondary C6 and tertiary C5 in thymine with approximately equal yields as well as the O4 adduct being a minor product.

The Cell and the Sum of Its Parts: Patterns of Complexity in Biosignatures as Revealed by Deep UV Raman Spectroscopy.

The next NASA-led Mars mission (Mars 2020) will carry a suite of instrumentation dedicated to investigating Martian history and the in situ detection of potential biosignatures. SHERLOC, a deep UV Raman/Fluorescence spectrometer has the ability to detect and map the distribution of many organic compounds, including the aromatic molecules that are fundamental building blocks of life on Earth, at concentrations down to 1 ppm. The mere presence of organic compounds is not a biosignature: there is widespread distribution of reduced organic molecules in the Solar System. Life utilizes a select few of these molecules creating conspicuous enrichments of specific molecules that deviate from the distribution expected from purely abiotic processes. The detection of far from equilibrium concentrations of a specific subset of organic molecules, such as those uniquely enriched by biological processes, would comprise a universal biosignature independent of specific terrestrial biochemistry. The detectability and suitability of a small subset of organic molecules to adequately describe a living system is explored using the bacterium Escherichia coli as a model organism. The DUV Raman spectra of E. coli cells are dominated by the vibrational modes of the nucleobases adenine, guanine, cytosine, and thymine, and the aromatic amino acids tyrosine, tryptophan, and phenylalanine. We demonstrate that not only does the deep ultraviolet (DUV) Raman spectrum of E. coli reflect a distinct concentration of specific organic molecules, but that a sufficient molecular complexity is required to deconvolute the cellular spectrum. Furthermore, a linear combination of the DUV resonant compounds is insufficient to fully describe the cellular spectrum. The residual in the cellular spectrum indicates that DUV Raman spectroscopy enables differentiating between the presence of biomolecules and the complex uniquely biological organization and arrangements of these molecules in living systems. This study demonstrates the ability of DUV Raman spectroscopy to interrogate a complex biological system represented in a living cell, and differentiate between organic detection and a series of Raman features that derive from the molecular complexity inherent to life constituting a biosignature.

Electronic Relaxation Dynamics of UV-Photoexcited 2-Aminopurine-Thymine Base Pairs in Watson-Crick and Hoogsteen Conformations.

The fluorescent analogue 2-aminopurine (2AP) of the canonical nucleobase adenine (6-aminopurine) base-pairs with thymine (T) without disrupting the helical structure of DNA. It therefore finds frequent use in molecular biology for probing DNA and RNA structures and conformational dynamics. However, detailed understanding of the processes responsible for fluorescence quenching remains largely elusive on a fundamental level. Although attempts have been made to ascribe decreased excited-state lifetimes to intrastrand charge-transfer and stacking interactions, possible influences from dynamic interstrand H-bonding have been widely ignored. Here, we investigate the electronic relaxation of UV-excited 2AP·T in Watson-Crick (WC) and Hoogsteen (HS) conformations. Although the WC conformation features slowed-down, monomer-like electronic relaxation in τ ∼ 1.6 ns toward ground-state recovery and triplet formation, the dynamics associated with 2AP·T in the HS motif exhibit faster deactivation in τ ∼ 70 ps. As recent research has revealed abundant transient interstrand H-bonding in the Hoogsteen motif for duplex DNA, the established model for dynamic fluorescence quenching may need to be revised in the light of our results. The underlying supramolecular photophysical mechanisms are discussed in terms of a proposed excited-state double-proton transfer as an efficient deactivation channel for recovery of the HS species in the electronic ground state.

Biocompatible organic-inorganic hybrid materials based on nucleobases and titanium developed by molecular layer deposition.

We have constructed thin films of organic–inorganic hybrid character by combining titanium tetra-isopropoxide (TTIP) and the nucleobases thymine, uracil or adenine using the molecular layer deposition (MLD) approach. Such materials have potential as bioactive coatings, and the bioactivity of these films is described in our recent work [Momtazi, L.; Dartt, D. A.; Nilsen, O.; Eidet, J. R. J. Biomed. Mater. Res., Part A 2018, 106, 3090–3098. doi:10.1002/jbm.a.36499]. The growth was followed by in situ quartz crystal microbalance (QCM) measurements and all systems exhibited atomic layer deposition (ALD) type of growth. The adenine system has an ALD temperature window between 250 and 300 °C, while an overall reduction in growth rate with increasing temperature was observed for the uracil and thymine systems. The bonding modes of the films have been further characterized by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy and X-ray diffraction, confirming the hybrid nature of the as-deposited films with an amorphous structure where partial inclusion of the TTIP molecule occurs during growth. The films are highly hydrophilic, while the nucleobases do leach in water providing an amorphous structure mainly of TiO2 with reduced density and index of refraction.

Radical pathways for the formation of non-canonical nucleobases in prebiotic environments.

Due to the inability of canonical nucleobases (adenine, uracil, guanine and cytosine) to spontaneously form ribonucleosides and base pairs in free form in solution, RNA is believed to be preceded by a primitive information polymer (preRNA). The preRNA is proposed to contain non-canonical, heterocyclic bases that possess the above-mentioned capabilities. An extensive search for such candidate heterocycles has recently revealed that barbituric acid (BA), melamine (MM) and 2,4,6-triaminopyrimidine (TAP) have the capability to spontaneously form ribonucleosides and supramolecular assemblies that are held by Watson–Crick type hydrogen-bonded base pairs involving BA, MM, TAP and cyanuric acid (CA) heterocycles. However, despite this evidence, the prebiotic formation pathways of these heterocycles have not been fully explored. Further, for these heterocycles to interact and assemble into informational polymers under prebiotic conditions, it is expected that they should have formed in the proximity of each other. In this context, the present work employs density functional theory to propose the associated radical based formation pathways starting from cyanamide. Our pathways suggest that cyanamide, its derivatives (malonic acid and urea) and malononitrile can form BA, MM, CA and TAP in the presence of ammonia and hydroxyl radicals. In addition to originating from a common precursor, similarities in the highest reaction barriers (13 to 20 kcal mol−1) obtained for these pathways suggest that these heterocycles may likely form under similar conditions. Specifically, these pathways are relevant to high energy events such as meteoritic impact during the late heavy bombardment period on the early earth, which would have created conditions where radicals might have formed in reasonable concentrations. Overall, the present study emphasizes the importance of cyanamide in prebiotic heterocycle formation.

Tracking the origin of photostability in purine nucleobases: the photophysics of 2-oxopurine.

This work scrutinizes the relaxation mechanism of 2-oxopurine. Contrary to its ancestor, purine, which is a UVC chromophore, 2-oxopurine shows a red-shifted absorption spectrum centered in the UVA region. In 2-oxopurine, relaxation along the ππ* spectroscopic state directs the population from the Franck-Condon (FC) region towards a minimum, which acts as a crossroad for the further decay of the system either to triplet states or, alternatively, to the ground state through a C6-puckered S1/S0 funnel. A comparison of the optical properties and excited state potential energy surfaces of purine, 2-oxopurine, 2-aminopurine, 6-oxopurine and adenine, allows establishing how the position and nature of substituent tune the photophysics of purine. For this series, we conclude that both C2 and C6 substitution redshift the absorption spectrum of purine, with 2-oxo substitution exhibiting the largest shift. An important exception is the canonical nucleobase adenine, which presents a blue shifted absorption spectrum. The topography of purine's ππ* potential energy surface experiences major changes when functionalized at the C6 position. In particular, the disappearance of the minimum along the ππ* potential energy surface efficiently funnels the excited state population from the FC region to the ground state and increases the photostability of 6-aminopurine (adenine) and 6-oxopurine (hypoxanthine) nucleobases.

Perubahan Panjang Lokalisasi dan Kerapatan Keadaan Elektron pada Molekul DNA Poli(dA)-Poli(dT) Karena Medan Magnet

The localization length and the Density Of State (DOS) of electron in a Poly(dA)-Poly(dT) DNA molecule at two temperatures have been calculated for several values of magnetic field. The calculation are carried out on a DNA molecule model that consists of adenine (A) and Thymine (T) nucleobases and sugar-phosphate backbone . The DNA molecule is modeled in tight binding Hamiltonian approach with semi empiri cal Slater-Koster theory and Peierls phase factor for introducing the effect of temperature and magnetic field, respectively . In the model, electron is allowed to move between nucleobase sites, backbode sites, and between backbone site and nucleobase site. The localization length is obtained from the smallest Lyapunov exponent which is calculated using transfer matri x method along with Gram-Schmidt ort h onormali zation procedure . The DOS is calculated using Green ’s function method by taking into account the presence of metallic electrode at both ends of the DNA molecule . The localization length and the DOS change as a result of the change in electron wave phase due to magnetic field. The change is observed at both temperature used in the study, but the change at lower temperature is larger than the one at higher temperature. Thermally agitated vibrational twisting motion perturbs electron motion in the DNA molecule such that the influence of magnetic field on the localization length and the DOS of electron at higher temperature becomes smaller.

UV Absorption and Magnetic Circular Dichroism Spectra of Purine, Adenine, and Guanine: A Coupled Cluster Study in Vacuo and in Aqueous Solution.

The absorption and magnetic circular dichroism (MCD) spectra of purine and of the purine nucleobases adenine and guanine have been calculated in gas phase at the Coupled Cluster Singles and Doubles (CCSD) and Resolution-of-Identity Singles and Approximate Doubles (RI-CC2) levels of theory. Exploiting a new development in the TURBOMOLE program package for computing vertical excitation energies and Faraday [Formula: see text] terms in an implicit solvent approximated by the conductor-like screening model (COSMO) at the CC2 level, we have investigated the solvent effects on the relative positions of the ππ* and nπ* electronic transitions in these three molecules and compared them to the corresponding vacuum results. In the case of adenine, we also included specific solvent effects with a small water cluster. The spectra obtained with the implicit model COSMO are in qualitative agreement with those obtained with explicit water molecules both with and without the inclusion of the bulk solvent effects via the continuum solvent model. This suggests that the inclusion of the electrostatic contributions of the solvent can provide a sufficiently accurate description of the absorption spectra for adenine. The results for purine, adenine, and guanine show that, after the inclusion of bulk solvation, the ππ* states shift to lower energies while at the same time nπ* states show a reversed behavior. The computed MCD spectra show the characteristic bisignate profile found experimentally in all cases, despite, for adenine, remarkable differences in the origin of the individual peaks for different computational methods. Therefore, the ability (or inability) of MCD to determine the relative stability of the La and Lb states is critically reassessed. According to our best estimate for adenine in aqueous solution, the La state is more stable than Lb.

High performance thin layer chromatography hyphenated with electrospray mass spectrometry for evaluation of nucleobases in two traditional Chinese medicinal mushrooms: A metabolomic approach

Present paper describes the application of a recently developed method for the determination of six nucleobases (thymine, uracil, adenine, cytosine, guanine and guanosine), by high performance thin layer chromatography (HPTLC) in Ganoderma lucidum (GL) and Cordyceps sinensis (CS) - two mushrooms that have been widely revered in traditional Chinese medicines. The method used a simple mobile phase constituted of dicholoromethane-methanol-formic acid (8:2.25:0.8, v/v/v). Validation of the method according to USP guidelines proved the method to be accurate (97.1–99.9%) and precise (1.8–5.2% RSD). Results confirmed the abundance of nucleobases in various extracts of GL and CS wherein the aqueous extracts of GL and ethanolic extracts of CS were found to have the maximum nucleobase content. Identification of nucleobases in the samples was reconfirmed by hyphenated HPTLC-MS technique. HPTLC data were further processed by chemometric tools like heat maps, cluster dendrograms and principal component analysis for drawing relatability patterns among the samples. Since both GL and CS are well known for their therapeutic applications, nucleobase profiling in these medicinal mushrooms will provide an essential lead in establishing their use in the development of drug formulations.

Theophylline alkaloid as glue of paddle-wheel copper(II)-adenine entities to afford a rhomboid chain

This work is aimed at the analysis of the interactions that drive the assembling of coordination metal-organic polymers based on biological molecules. Single-crystal X-ray diffraction data show that the compound 1D-{[Cu2(μ-ade)4(H2O)2]·2[Cu(theoph)2]·∼10H2O}n (1) contains neutral rhomboid shaped chains sustained by the tridentate μ3-κN3:κN7:κN9 coordination mode of the adenine nucleobase. These chains are formed by dimeric copper/adeninato (ade) cores doubly bridged by monomeric copper/theophyllinato (theoph) entities with the alkaloid acting as peripheral ligand. The lack of direct intermolecular nucleobase···nucleobase interactions, due to their disruption by the crystallization water molecules, does not provide a highly porous material, but the irregular shape of the polymeric chain hinders their packing and allows the presence of a moderate amount of voids (16% of the unit cell volume) in good accordance with its adsorption capacity of 0.38 mmol CO2/g at 273 K. Thermogravimetric and variable temperature X-ray diffraction analyses show that the compound retains its structure up to 110 °C whereas above this temperature the release of the coordination water molecules produces a significant loss of crystallinity. Magnetic measurements indicate an overall antiferromagnetic behavior with a J value of −267 cm−1 within the dimeric entity.

Synthesis of graphitic carbon nitride with large specific surface area via copolymerizing with nucleobases for photocatalytic hydrogen generation

Sponge-like porous carbon nitrides with large specific surface area are prepared by a green and facile synthesis method using melamine and biological reagent nucleobases (adenine, guanine, cytosine, thymidine and uracil) as precursors. The excellent biocompatibility and hydrogen bonding tendency of the nucleobase provides multiple binding sites for melamine, thus exhibiting preferable performance (5100.5 μmol h−1 g−1) than the traditional molecular as precursor. The enhanced photocatalytic performance benefits from the significantly increased specific surface area and average fluorescence lifetime as well as reduced bandgap, which leads to more exposed active sites, suppressed radiative recombination of photo-excited charge carriers, and improved light absorption. In this work, the effect of different nucleobases in increasing the catalytic activity is emphatically discussed in terms of spatial interaction forces and a matching hydrogen bonding mechanism is proposed. Photocatalytic hydrogen evolution experiments further demonstrate the enormous potential application of biomolecules in the modification of two-dimensional materials.