Hydroxy Amino Acids Research Articles

“A classical method for synthesis of epoxy-amino acid nanostructure composites with an enhanced property”

Here we have introduced the novel method for the processing of amino acid and epoxy composite preparation. Which generates new nanostructure composites from the stoichiometric combination of both amino acid and epoxy resin. Here the active functional hydroxy amino acids as well as amine were utilized as one of the reagents. The advantage for the duel functional group plays an important role in final composite for its strength and structural morphology of nanocomposites. The dispersion ability of this nanostructure was tested by using a non-conventional sonication method for coating formulation. The particle size plays an important role while dispersing the composites into the matrix. Organic solvents have been used during the composite preparation which provides synergy for the chemical combination. SEM images suggest the continuous dispersion and intact of the nanostructure nature of the final composites in the polymer matrix. DSC/TGA thermal degradation suggested the composite pattern with reference to the thermal decay events also the covalent bonding structure is also analyzed. Similarly, the strength of polymer nanocomposite was verified with the mechanical properties with ASTM standards. Eventually the presents of amino acid functionality in final composites structure breeds the antimicrobial nature.

Stereochemistry of aminoacylated cardiolipins and phosphatidylglycerols from bacteria.

Hydrophilic interaction liquid chromatography (HILIC) connected with electrospray high-resolution tandem mass spectrometry (MS) was used for the analysis of unusual amino acid (AA) substituted phosphatidylglycerols (PG) and cardiolipins (CL) in mesophilic and thermophilic bacteria. Individual peaks from the lipid class separation by HILIC were isolated and hydrolyzed to determine the absolute configuration of the aminoacyl side chain. The configuration of the aminoacyl side chain was assigned by indirect liquid chromatography (LC) enantiomer separation after the hydrolysis of the aminoacylated (aminoacyl) lipids using N-(4-nitrophenoxycarbonyl)-l-phenylalanine 2-methoxyethyl ester as chiral derivatizing agent and reversed phase LC-MS for analysis. When two chromatographic methods were combined, less common AAs, such as d-allo-Ile and d-allo-Thr, were identified. The taxonomic classification of bacteria showed that bacteria of the family Bacillaceae (Bacillus and Geobacillus) produce branched-chain AAs, that is, d-allo-Ile, d-Ile, and d-Leu. These AAs were present only in the genera Bacillus and Geobacillus and not in Alicyclobacillus acidoterrestris (family Alicyclobacillaceae). On the contrary, hydroxy AAs, that is, l- and d-Thr, and l- and d-allo-Thr, were identified as aminoacyl-PG and aminoacyl-CL in A. acidoterrestris and were not present in the genera Bacillus and Geobacillus. Therefore, the complete analysis made it possible to identify the stereochemistry of AAs in aminoacyl PGs and CLs and use this fact for chemotaxonomy.

Therapeutic Copolymer from Salicylic Acid and l-Phenylalanine as a Nanosized Drug Carrier for Orthotopic Breast Cancer with Lung Metastasis.

Nanoparticle (NP)-mediated drug delivery systems are promising for treating various diseases. However, clinical translation has been delayed by a variety of limitations, such as weak drug loading, nonspecific drug leakage, lack of bioactivity, and short blood circulation. These issues are in part due to the unsatisfactory function of biomaterials for nanocarriers. In addition, the synthesis procedures of drug carrier materials, especially polymers, were usually complicated and led to high cost. In this report, a bioactive copolymer of hydroxy acid and amino acid, poly(salicylic acid-co-phenylalanine) (PSP), was developed for the first time via a one-step rapid and facile synthesis strategy. The PSP could self-assemble into NPs (PSP-NPs) to co-load relatively hydrophilic sphingosine kinase 1 inhibitor (PF543 in HCl salt format) and highly hydrophobic paclitaxel (PTX) to form PF543/PTX@PSP-NPs with efficient dual drug loading. Encouragingly, PF543/PTX@PSP-NPs showed long blood circulation, good stability, and high tumor accumulation, leading to significantly enhanced therapeutic effects on breast cancer. Furthermore, PF543/PTX@PSP-NPs could additionally suppress the lung metastasis of breast cancer, and more importantly, the PSP-NPs themselves as therapeutic nanocarriers also showed an anti-breast cancer effect. With these combined advantages, this new polymer and corresponding NPs will provide valuable insights into the development of new functional polymers and nanomedicines for important diseases.

Recent Advances in the Hydroxylation of Amino Acids and Its Derivatives

Hydroxy amino acids (HAAs) are of unique value in the chemical and pharmaceutical industry with antiviral, antifungal, antibacterial, and anticancer properties. At present, the hydroxylated amino acids most studied are tryptophan, lysine, aspartic acid, leucine, proline, etc., and some of their derivatives. The hydroxylation of amino acids is inextricably linked to the catalysis of various biological enzymes, such as tryptophan hydroxylase, L-pipecolic acid trans-4-hydroxylase, lysine hydroxylase, etc. Hydroxylase conspicuously increases the variety of amino acid derivatives. For the manufacture of HAAs, the high regioselectivity biocatalytic synthesis approach is favored over chemical synthesis. Nowadays, the widely used method is to transcribe the hydroxylation pathway of various amino acids, including various catalytic enzymes, into Corynebacterium glutamicum or Escherichia coli for heterologous expression and then produce hydroxyamino acids. In this paper, we systematically reviewed the biosynthetic hydroxylation of aliphatic, heterocyclic, and aromatic amino acids and introduced the basic research and application of HAAs.

Antibacterial and Antimycotic Properties of Modified Carbon Sorbents

The aim of the work was to study the biological activity of modifiers and carbon sorbent samples modified by them in relation to some types of microorganisms.Material and methods. The carbon sorbent under study and the modified samples were obtained at the Center of New Chemical Technologies BIC. Glycolic acid, lactic acid, glycine, and glutamic acid were used as modifiers. Strains of Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae 418, Esherichia coli ATCC 25922, Candida albicans (clinical strain) were used as test cultures. The test sample was placed in the wells of a sterile plate, then a working suspension of the test culture was added in the amount of 2.0 ml until completely wet 1:1. The survival of microorganisms was determined by quantitative inoculation from each well of the «sample — microorganism» mixture on Petri dishes with simple nutrient agar using the sector crop method (Gold). The culture species were confirmed by studying their cultural, morphological, and biochemical properties.Results. The conducted studies have demonstrated high antibacterial and antimycotic activity of carbon sorbent samples modified with hydroxyl acids in relation to the most common opportunistic pathogens of pyoinflammatory diseases of bacterial and fungal nature in comparison with the initial sorbent sample. The carbon sorbent modified with lactic acid oligomer showed the highest antibacterial and antimycotic activity.Conclusion. High antibacterial and antimycotic activity of carbon sorbent samples modified with hydroxy acids and amino acids in relation to the most common opportunistic pathogens of pyoinflammatory diseases of bacterial and fungal nature was established in comparison with the initial sample of the sorbent. The carbon sorbent sample modified with amino acids has a pronounced antibacterial effect against all studied bacterial test strains, but exhibits weak antimycotic properties. The use of modified carbon sorbents is a promising direction for the application therapy of pyoinflammatory infections.

Marine Organisms as a Prolific Source of Bioactive Depsipeptides

Depsipeptides, an important group of polypeptides containing residues of hydroxy acids and amino acids linked together by amide and ester bonds, have potential applications in agriculture and medicine. A growing body of evidence demonstrates that marine organisms are prolific sources of depsipeptides, such as marine cyanobacteria, sponges, mollusks, microorganisms and algae. However, these substances have not yet been comprehensively summarized. In order to enrich our knowledge about marine depsipeptides, their biological sources and structural features, as well as bioactivities, are highlighted in this review after an extensive literature search and data analysis.

Zinc-Catalyzed Desymmetric Reduction To Form Hydroxylated Tetrasubstituted Amino Acids

Key words zinc catalysis - desymmetrization - reduction - hydroxy amino acids

Chiral 3D metal–organic frameworks with zinc and hydroxy-amino acids

Chiral 3D metal–organic frameworks with zinc and hydroxy-amino acids

Modifying a Hydroxyl Patch in Glucagon-like Peptide 1 Produces Biased Agonists with Unique Signaling Profiles.

Glucagon-like peptide-1 (GLP-1) lowers blood glucose by inducing insulin but also has other poorly understood properties. Here, we show that hydroxy amino acids (Thr11, Ser14, Ser17, Ser18) in GLP-1(7-36) act in concert to direct cell signaling. Mutating any single residue to alanine removes one hydroxyl group, thereby reducing receptor affinity and cAMP 10-fold, with Ala11 or Ala14 also reducing β-arrestin-2 10-fold, while Ala17 or Ala18 also increases ERK1/2 phosphorylation 5-fold. Multiple alanine mutations more profoundly bias signaling, differentially silencing or restoring one or more signaling properties. Mutating three serines silences only ERK1/2, the first example of such bias. Mutating all four residues silences β-arrestin-2, ERK1/2, and Ca2+ maintains the ligand and receptor at the membrane but still potently stimulates cAMP and insulin secretion in cells and mice. These novel findings indicate that hydrogen bonding cooperatively controls cell signaling and highlight an important regulatory hydroxyl patch in hormones that activate class B G protein-coupled receptors.

Enantioselective Determination of Hydroxy Amino Acids in Japanese Traditional Amber Rice Vinegars

A fully-automated two-dimensional (2D) HPLC system for the determination of serine (Ser), threonine (Thr) and allo-threonine (aThr) enantiomers was developed. The system was validated and applied to the determination of the target hydroxy amino acid enantiomers in vinegar samples including the Japanese traditional amber rice vinegar. The Japanese traditional amber rice vinegar is one of the typical natural fermented products containing high levels of D-amino acids, and the clarification of the amounts of hydroxy amino acid enantiomers is expected. For the on-line 2D-HPLC system, a narrowbore ODS column (Singularity RP18, 1.0 x 250 mm) was used in the first dimension, and an originally-designed Pirkle-type chiral stationary phase (Singularity CSP-013S, 1.5 x 250 mm) was utilized in the second dimension. The target hydroxy amino acids were derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) and detected by their fluorescence (ex. 470 nm, em. 530 nm). The concentrations and the %D values were compared among a grain vinegar, a widely-distributed black vinegar and Japanese traditional amber rice vinegars (fermented/aged 1 or 5 years by microorganisms in an earthenware jar). The amounts of hydroxy amino acid enantiomers were low (0.21-0.38 μmol/mL, only L-forms) in the grain vinegar, and relatively high amounts of the L-forms were observed (1.05-1.61 μmol/mL) in the widely-distributed black vinegar. On the other hand, clear peaks of the D-forms (0.16-0.86 μmol/mL for D-Ser, 0.02-0.11 μmol/mL for D-aThr) as well as high amounts of the L-forms (2.27-2.51 μmol/mL for L-Ser, 1.85-2.10 μmol/mL for L-Thr) were observed in the Japanese traditional amber rice vinegars. The amounts of D-Ser and D-aThr clearly increased with increasing the fermentation/aging period. This is the first report showing the profiles of the hydroxy amino acid enantiomers simultaneously, and further investigations using various fermented food/beverage samples are expected.

Beyond Lysine Ubiquitination

The covalent attachment of ubiquitin to substrates controls virtually all aspects of the cell. With rare exceptions, ubiquitin was understood to exert its effects by becoming attached to the amino group of lysine residues within protein substrates. Recent discoveries from our lab and others have revealed that dedicated writers (E3 ligases) and erasers (DUBs) of non‐lysine ubiquitination are intrinsic to eukaryotes. This highlights that attachment to sites beyond lysine are physiologically and perhaps pathologically important. These E3s tend to be highly divergent from their established counterparts and “activity‐based” chemical biology approaches have been instrumental in identifying them. I will present work from my lab on technologies we have used to uncover unusual E3 ligases and the striking nature of their mechanism and substrate specificity. I will also discuss our characterisation of a small DUB family that is highly selective at removing ubiquitin from hydroxy amino acids. These new developments indicate that non‐lysine ubiquitination is an integral component of the ubiquitin system that is subject to sophisticated regulation.

Agonist-induced phosphorylation of orthologues of the orphan receptor GPR35 functions as an activation sensor

G protein-coupled receptor 35 (GPR35) is poorly characterized but nevertheless has been revealed to have diverse roles in areas including lower gut inflammation and pain. The development of novel reagents and tools will greatly enhance analysis of GPR35 functions in health and disease. Here, we used mass spectrometry, mutagenesis, and [32P] orthophosphate labeling to identify that all five hydroxy-amino acids in the C-terminal tail of human GPR35a became phosphorylated in response to agonist occupancy of the receptor and that, apart from Ser294, each of these contributed to interactions with arretin-3, which inhibits further G protein-coupled receptor signaling. We found that Ser303 was key to such interactions; the serine corresponding to human GPR35a residue 303 also played a dominant role in arrestin-3 interactions for both mouse and rat GPR35. We also demonstrated that fully phospho-site–deficient mutants of human GPR35a and mouse GPR35 failed to interact effectively with arrestin-3, and the human phospho-deficient variant was not internalized from the surface of cells in response to agonist treatment. Even in cells stably expressing species orthologues of GPR35, a substantial proportion of the expressed protein(s) was determined to be immature. Finally, phospho-site–specific antisera targeting the region encompassing Ser303 in human (Ser301 in mouse) GPR35a identified only the mature forms of GPR35 and provided effective sensors of the activation status of the receptors both in immunoblotting and immunocytochemical studies. Such antisera may be useful tools to evaluate target engagement in drug discovery and target validation programs.

Electrospun Silk Fibroin Scaffolds for Tissue Regeneration: Chemical, Structural, and Toxicological Implications of the Formic Acid-Silk Fibroin Interaction.

The dissolution of Bombyx mori silk fibroin (SF) films in formic acid (FA) for the preparation of electrospinning dopes is widely exploited to produce electrospun SF scaffolds. The SILKBridge® nerve conduit is an example of medical device having in its wall structure an electrospun component produced from an FA spinning dope. Though highly volatile, residual FA remains trapped into the bulk of the SF nanofibers. The purpose of this work is to investigate the type and strength of the interaction between FA and SF in electrospun mats, to quantify its amount and to evaluate its possible toxicological impact on human health. The presence of residual FA in SF mats was detected by FTIR and Raman spectroscopy (new carbonyl peak at about 1,725 cm−1) and by solid state NMR, which revealed a new carbonyl signal at about 164.3 ppm, attributed to FA by isotopic 13C substitution. Changes occurred also in the spectral ranges of hydroxylated amino acids (Ser and Thr), demonstrating that FA interacted with SF by forming formyl esters. The total amount of FA was determined by HS-GC/MS analysis and accounted for 247 ± 20 μmol/g. The greatest part was present as formyl ester, a small part (about 3%) as free FA. Approximately 17% of the 1,500 μmol/g of hydroxy amino acids (Ser and Thr) theoretically available were involved in the formation of formyl esters. Treatment with alkali (Na2CO3) succeeded to remove the greatest part of FA, but not all. Alkali-treated electrospun SF mats underwent morphological, physical, and mechanical changes. The average diameter of the fibers increased from about 440 nm to about 480 nm, the mat shrunk, became stiffer (the modulus increased from about 5.5 MPa to about 7 MPa), and lost elasticity (the strain decreased from about 1 mm/mm to about 0.8 mm/mm). Biocompatibility studies with human adult dermal fibroblasts did not show significant difference in cell proliferation (313 ± 18 and 309 ± 23 cells/mm2 for untreated and alkali-treated SF mat, respectively) and metabolic activity. An in-depth evaluation of the possible toxicological impact of residual FA was made using the SILKBridge® nerve conduit as case study, following the provisions of the ISO 10993-1 standard. The Potential Patient Daily Intake, calculated from the total amount of FA determined by HS-GC/MS, was 2.4 mg/day and the Tolerable Exposure level was set to 35.4 mg/day. This allowed to obtain a value of the Margin of Safety of 15, indicating that the amount of FA left on SF mats after electrospinning does not raise concerns for human health.

Extraterrestrial hydroxy amino acids in CM and CR carbonaceous chondrites

AbstractThe abundances, distributions, and enantiomeric ratios of a family of three‐ and four‐carbon hydroxy amino acids (HAAs) were investigated in extracts of five CM and four CR carbonaceous chondrites by gas chromatography‐mass spectrometry analyses. HAAs were detected in both the acid hydrolysates of the hot water extracts and the 6 M HCl extracts of all the CM and CR chondrites analyzed here with total hot water and HCl extractable HAA concentrations ranging from 6.94 to 315 nmol g−1. The HAA analyses performed in this study revealed: (1) the combined (hot water + HCl) extracts of CR2 chondrites contained greater abundances of α‐HAAs than that of CM2 chondrites and (2) the combined extracts of CM and CR chondrites contained roughly similar abundances of β‐ and γ‐HAAs. Application of the new GC‐MS method developed here resulted in the first successful chromatographic resolution of the enantiomers of an α‐dialkyl HAA, d,l‐α‐methylserine, in carbonaceous chondrite extracts. Meteoritic α‐methylserine was found to be mostly racemic within error and did not show l‐enantiomeric excesses correlating with the degree of aqueous alteration, a phenomenon observed in meteoritic isovaline, another α‐dialkyl amino acid. The HAAs identified in CM and CR chondrite extracts could have been produced during parent body alteration from the Strecker cyanohydrin reaction (for α‐HAAs) and an ammonia‐involved formose‐like reaction (for β‐, and γ‐HAAs).

Novel Strategy for Untargeted Chiral Metabolomics using Liquid Chromatography-High Resolution Tandem Mass Spectrometry.

Stereospecific recognition of metabolites plays a significant role in the detection of potential disease biomarkers thereby providing new insights in diagnosis and prognosis. D-Hdroxy/amino acids are recognized as potential biomarkers in several metabolic disorders. Despite continuous advances in metabolomics technologies, the simultaneous measurement of different classes of enantiomeric metabolites in a single analytical run remains challenging. Here, we develop a novel strategy for untargeted chiral metabolomics of hydroxy/amine groups (-OH/-NH2) containing metabolites, including all hydroxy acids (HAs) and amino acids (AAs), by chiral derivatization coupled with liquid chromatography-high resolution tandem mass spectrometry (LC-HR-MS/MS). Diacetyl-tartaric anhydride (DATAN) was used for the simultaneous derivatization of-OH/-NH2 containing metabolites as well as the resulting diastereomers, and all the derivatized metabolites were resolved in a single analytical run. Data independent MS/MS acquisition (DIA) was applied to positively identify DATAN-labeled metabolites based on reagent specific diagnostic fragment ions. We discriminated chiral from achiral metabolites based on the reversal of elution order of D and L isomers derivatized with the enantiomeric pair (±) of DATAN in an untargeted manner. Using the developed strategy, a library of 301 standards that consisted of 214 chiral and 87 achiral metabolites were separated and detected in a single analytical run. This approach was then applied to investigate the enantioselective metabolic profile of the bone marrow (BM) and peripheral blood (PB) plasma samples from patients with acute myeloid leukemia (AML) at diagnosis and following completion of the induction phase of chemotherapeutic treatment. The sensitivity and selectivity of the developed method enabled the detection of trace levels of the D-enantiomer of HAs and AAs in primary plasma patient samples. Several of these metabolites were significantly altered in response to chemotherapy. The developed LC-HR-MS method entails a valuable step forward in chiral metabolomics.

Conservation of the HBV RNA element epsilon in nackednaviruses reveals ancient origin of protein-primed reverse transcription

Hepadnaviruses, with the human hepatitis B virus as prototype, are small, enveloped hepatotropic DNA viruses which replicate by reverse transcription of an RNA intermediate. Replication is initiated by a unique protein-priming mechanism whereby a hydroxy amino acid side chain of the terminal protein (TP) domain of the viral polymerase (P) is extended into a short DNA oligonucleotide, which subsequently serves as primer for first-strand synthesis. A key component in the priming of reverse transcription is the viral RNA element epsilon, which contains the replication origin and serves as a template for DNA primer synthesis. Here, we show that recently discovered non-enveloped fish viruses, termed nackednaviruses [C. Lauber et al., Cell Host Microbe 22, 387-399 (2017)], employ a fundamentally similar replication mechanism despite their huge phylogenetic distance and major differences in genome organization and viral lifestyle. In vitro cross-priming studies revealed that few strategic nucleotide substitutions in epsilon enable site-specific protein priming by heterologous P proteins, demonstrating that epsilon is functionally conserved since the two virus families diverged more than 400 Mya. In addition, other cis elements crucial for the hepadnavirus-typical replication of pregenomic RNA into relaxed circular double-stranded DNA were identified at conserved positions in the nackednavirus genomes. Hence, the replication mode of both hepadnaviruses and nackednaviruses was already established in their Paleozoic common ancestor, making it a truly ancient and evolutionary robust principle of genome replication that is more widespread than previously thought.

The effect of temperature on the kinetics of enhanced amide bond formation from lactic acid and valine driven by deep eutectic solvents.

Deep eutectic solvents have been found to facilitate the copolymerization of hydroxy acids and amino acids through an ester-amide exchange reaction, and to drive the formation of amino acid-enriched oligomers with peptide backbones. The complexity of oligomer distribution is significantly reduced in deep eutectic solvents and amide-linked oligomers can be selectively produced. In the present study, we investigated the kinetics of amide bond formation in deep eutectic solvents to understand how the solvents regulate the pathways of complex copolymerization. A mathematical model successfully simulated the reaction of a lactic acid/valine mixture in deep eutectic solvents at different temperatures and provided insight into the activation energy of each step. Our findings indicated that the esterification and the evaporation of hydroxy acids were greatly suppressed in deep eutectic solvents because of the strong interaction between the quaternary ammonium salts and the hydroxy acids. In contrast, the ester-amide exchange reaction in deep eutectic solvents was significantly enhanced by lowering the activation entropies. The synergic effect of reduced esterification and increased exchange leads to amino acid-enriched oligomers with high yield and high selectivity. Furthermore, the reduced evaporation of hydroxy acids in deep eutectic solvents may preserve limited reactants in the prebiotic scenario. These results reveal deep eutectic solvents as sustainable media for the simple synthesis of amide bonds.

Enantioselective Aza‐Diels Alder reaction catalyzed by clay supported Schiff base complex†

AbstractClay supported catalysts based on 2‐ hydroxy naphthaldehyde and amino acids, their copper and titanium complexes have been described. The catalysts were found to be active toward the synthesis of pyrano‐, furanoquinolines through Aza‐Diels Alder reaction. The catalysts gave good yield and high enantioselectivity. The catalysts were environmentally friendly, economical, synthetically robust and reusable.

2-Ketoglutarate-Generated In Vitro Enzymatic Biosystem Facilitates Fe(II)/2-Ketoglutarate-Dependent Dioxygenase-Mediated C-H Bond Oxidation for (2s,3r,4s)-4-Hydroxyisoleucine Synthesis.

Fe(II)/2-ketoglutarate-dependent dioxygenase (Fe(II)/2-KG DO)-mediated hydroxylation is a critical type of C–H bond functionalization for synthesizing hydroxy amino acids used as pharmaceutical raw materials and precursors. However, DO activity requires 2-ketoglutarate (2-KG), lack of which reduces the efficiency of Fe(II)/2-KG DO-mediated hydroxylation. Here, we conducted multi-enzymatic syntheses of hydroxy amino acids. Using (2s,3r,4s)-4-hydroxyisoleucine (4-HIL) as a model product, we coupled regio- and stereo-selective hydroxylation of l-Ile by the dioxygenase IDO with 2-KG generation from readily available l-Glu by l-glutamate oxidase (LGOX) and catalase (CAT). In the one-pot system, H2O2 significantly inhibited IDO activity and elevated Fe2+ concentrations of severely repressed LGOX. A sequential cascade reaction was preferable to a single-step process as CAT in the former system hydrolyzed H2O2. We obtained 465 mM 4-HIL at 93% yield in the two-step system. Moreover, this process facilitated C–H hydroxylation of several hydrophobic aliphatic amino acids to produce hydroxy amino acids, and C–H sulfoxidation of sulfur-containing l-amino acids to yield l-amino acid sulfoxides. Thus, we constructed an efficient cascade reaction to produce 4-HIL by providing prerequisite 2-KG from cheap and plentiful l-Glu and developed a strategy for creating enzymatic systems catalyzing 2-KG-dependent reactions in sustainable bioprocesses that synthesize other functional compounds.

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds.

Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.