Use In Solid-phase Synthesis Research Articles

Synthesis of a benzotriazole azo dye phosphoramidite for labelling of oligonucleotides

The synthesis of a benzotriazole azo dye phosphoramidite and the subsequent use in solid phase synthesis of oligonucleotides is reported. The azo dye is shown as a surface enhanced resonance Raman label for oligonucleotides that is capable of immobilisation of the oligonucleotide on metal surfaces such as silver nanoparticles.

1-[2-[(5-Cyanopyridin-2-yl)amino]ethylamino]acetyl-2-(S)-pyrrolidinecarbonitrile: A Potent, Selective, and Orally Bioavailable Dipeptidyl Peptidase IV Inhibitor with Antihyperglycemic Properties

Dipeptidyl peptidase IV (DPP-IV) inhibition has the potential to become a valuable therapy for type 2 diabetes. We report the first use of solid-phase synthesis in the discovery of a new DPP-IV inhibitor class and a solution-phase synthesis that is practical up to the multikilogram scale. One compound, NVP-DPP728 (2), is profiled as a potent, selective, and short-acting DPP-IV inhibitor that has excellent oral bioavailability and potent antihyperglycemic activity.

A novel core-shell type polymer support for solid-phase peptide synthesis

Novel core-shell type resins with a highly cross-linked polystyrene (PS) core and a poly(ethylene glycol) (PEG) shell were prepared by suspension polymerization for use in solid-phase synthesis. All the resins were of bead type with a diameter of 50–200 μm. The loading capacities of the amino groups were 0.05–0.2 mmol/g resin and the thickness of the PEG shell was 2–4 μm. Compared with the other resins such as 1% cross-linked PS resin and TentaGel resin, the resins showed excellent performance in photolytic release of peptide product from photolabile linker.

Polymer bound iminodicarbonate: a new ammonia equivalent for solid-phase synthesis of primary amines

A polymer bound iminodicarbonate has been designed and its use in solid-phase synthesis of primary amines is reported.

Recent progress in the solid-phase synthesis of glycopeptide.

The recent understanding of the biological role of glycoproteins has brought about a demand for the highly homogeneous glycopeptides as the functional model for glycoproteins. Thus, much efforts have been made to establish easy and efficient method for glycopeptide synthesis. In this paper, we briefly review the recent advances in the synthesis of O- and N-linked glycopeptide based on the solid-phase method. In O-glycopeptide section, the preparation of glycosylated amino acid units with mucin type and other O-linked carbohydrate chains and their use for solid-phase synthesis are summarized. Other approaches, such as the glycosylation of resin bound peptide are also overviewed. In N-glycopeptide section, the synthesis using glycosylated amino acid units as well as other methods are described.

High-Resolution Magic Angle Spinning NMR Study of Resin-Bound Polyalanine Peptides

Polyalanine sequences of varying length and tethered to a solid support are studied in atomic detail by high-resolution magic angle spinning (HR MAS) NMR. At high densities, it is shown that aggregation of the sequences is at the origin of synthetic difficulties. Decreasing the peptide density by discharging the resin allows study of longer sequences without being hampered by aggregation, and α helix formation has been observed for the (Ala)12 sequence. This demonstrates that the combined use of solid phase synthesis and high resolution magic angle spinning NMR spectroscopy is a new tool that can be used advantageously in the study of aggregating structures

Convenient synthesis of glycosylated hydroxylysine derivatives for use in solid-phase peptide synthesis

δ- O-Glycosylated 9-fluorenylmethoxycarbonyl-hydroxylysine (Fmoc-Hyl) derivatives have been conveniently prepared by introduction of a β- d-galactopyranosyl group to copper-complexed Hyl[ε- tert-butyloxycarbonyl (Boc)] or Hyl[ε-allyloxycarbonyl (Aloc)], followed by decomposition of the copper complex and addition of an Fmoc group to the α-amino group. Fmoc-Hyl[ε-Boc, O-(2,3,4,6-tetra- O-acetyl-β- d-galactopyranosyl)] was used in the solid-phase synthesis of a type IV collagen derived sequence.

Recent advances in solid phase synthesis.

The use of solid phase synthesis continues to expand as chemists identify methodology that enables complex reactions. Recent efforts in this area have focused on new carbon-carbon bond forming reactions as well as a variety of heterocyclic systems. These examples are described along with updates on new linking strategies for solid phase synthesis.

ChemInform Abstract: Dipeptide Surrogates Containing Asparagine‐Derived Tetrahydropyrimidinones: Preparation, Structure, and Use in Solid Phase Synthesis.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Dipeptide Surrogates Containing Asparagine-Derived Tetrahydropyrimidinones: Preparation, Structure, and Use in Solid Phase Synthesis

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTDipeptide Surrogates Containing Asparagine-Derived Tetrahydropyrimidinones: Preparation, Structure, and Use in Solid Phase SynthesisJoseph P. Konopelski, Lubov K. Filonova, and Marilyn M. OlmsteadView Author Information Department of Chemistry and Biochemistry University of California, Santa Cruz, California 95064 Department of Chemistry, University of California Davis, California 95616 Cite this: J. Am. Chem. Soc. 1997, 119, 18, 4305–4306Publication Date (Web):May 7, 1997Publication History Received13 November 1996Published online7 May 1997Published inissue 1 May 1997https://doi.org/10.1021/ja9639271Copyright © 1997 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views219Altmetric-Citations17LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (109 KB) Get e-AlertsSupporting Info (3)»Supporting Information Supporting Information SUBJECTS:Amides,Amines,Monomers,Organic polymers,Peptides and proteins Get e-Alerts

An approach to enantiomerically pure inverse γ-turn mimetics for use in solid-phase synthesis

An inverse γ-turn mimetic, having a morpholin-3-one ring as the key structural unit, was prepared in enantiomerically pure form in seven steps and 37% overall yield starting from 2( R)-[1′( S)-azido-2′-phenylethyl]oxirane ( 3). The mimetic has side-chains corresponding to a Phe-Ala-Ala tripeptide but the synthetic route was designed to allow incorporation also of other side chains. Molecular mechanics calculations revealed that the torsional angles of the second residue of the mimetic were effectively locked into an inverse γ-turn like conformation.

Use of FT-IR Internal Reflection Spectroscopy in Combinatorial Chemistry

Combinatorial chemistry technologies for new-lead discovery and lead optimization have recently captured the imagination of the drug-discovery community. With the use of solid-phase synthesis on polymer substrates, vast numbers of molecules, so-called chemical libraries, will be readily accessible by these combinatorial approaches as potential sources of new leads for drug discovery.

Synthesis of aliphatic O-dimannosyl amino acid building blocks for solid-phase assembly of glycopeptide libraries

The preparation of α(1,2)-, α(1,3)- and α(1,6)-linked mannose disaccharides is described. The protected α-D-Man(1→3)-D-Man disaccharide was synthesized using the trichloroacetimidate method, while the Konigs–Knorr procedure was employed in the preparation of the 1→2- and 1→6-linked disaccharides. Glycosylation of Nα-Fmoc-Ser-OPfp, Nα-Fmoc-Thr-OPfp and Nα-Fmoc-Hyp-OPfp with the dimannosyl bromides afforded the activated building blocks, in moderate to high yield, for direct use in solid-phase synthesis of glycopeptide libraries.

Synthesis of redox derivatives of lysine and their use in solid-phase synthesis of a light-harvesting peptide

Redox-active amino acids were synthesized for incorporation into peptide assemblies to study photoinitiated electron or energy transfer. 4′-Methyl-2,2′-bipyridine-4-carboxylic acid was obtained in 72% yield by consecutive SeO 2 and Ag 2O oxidation without isolation of intermediates. The side chain ε-amino group of Boc- l-lysine methyl ester or γ-carboxyl group of Boc- l-glutamic acid α-methyl ester was coupled to a redox moiety (transition-metal chromophore, electron donor, electron acceptor, metal ligand, or triplet-energy transmitter) using 4-(dimethylamino)pyridine, (1-benzotriazoleoxy)tris(dimethylamino)phosphonium hexafluorophosphate, N-methylmorpholine, and 1-hydroxybenzotriazole. Use of one equivalent of 4-(dimethylamino)pyridine provided the amide coupling product in 80–97% isolated yield. Selective hydrolysis of the methyl esters with lithium hydroxide provided the redox Boc-amino acids in 70–98% yield. These redox modules are suitable for solid-phase assembly of light-harvesting peptides, as illustrated by the synthesis of the partially α-helical 11-residue redox triad that contains a phenothiazine electron donor, a ruthenium(II)tris(bipyridine) chromophore, and an anthraquinone electron acceptor. Upon laser excitation at 420 nm, the peptide triad underwent photoinduced electron transfer to create a charge-separated state with a lifetime of 53 ns and decayed with a first-order rate constant of 1.9 × 10 8 s −1.

Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

Synthesis and characterisation of porous polymers

AbstractState‐of‐the‐art electron microscopic studies have been made of the ultrastructure of a matrix of specifically prepared styrene‐divinylbenzene resin sorbents. Image analysis methods have been applied to quantify the porous morphology of these resins in the “dry”, “freeze‐dried” and “frozen” states. Significant swelling has been demonstrated in the wet state. Highly porous Polyhipe® monoliths have been prepared and used to produce a polyamide‐impregnated composite support for use in solid phase synthesis of peptides. The composite shows good pressure resistance and allows high yields of pure peptides to be achieved. Polyhipe® polymers with very high surface areas (up to 350 m2g−1) have been prepared by applying the methodologies of porous particulate resin production to achieve highly porous walls in the Polyhipe® structures. Finally, novel procedures are described for the preparation of porous particulate polyimides and polybenzimidazoles involving a paraffin oil dispersion methodology. These thermooxidatively stable resins have been prepared with modest surface areas of ∼30 m2g−1 and offer good prospects for use as supports for alkene transition metal complex oxidation catalysts.

Studies on the Formation of the Internucleotidic Bond in RNA Synthesis Using Dialkylamino Phosphoroamidites

Abstract Several N,N-dialkylamlno-cyanoethyl-phosphoroamidites were tested for use in solid-phase synthesis of homo-uridine RNA fragments. N-ethyl-N-me-thylamino protection gave the best results. The corresponding monomer is stable for several months and an average coupling yield of 97 % was obtained after 4 minutes of condensation using this agent.

O-aryl phosphoramidites: synthesis, reactivity and evaluation of their use for solid-phase synthesis of oligonucleotides

Deoxynucleoside 3'-O-arylphosphoramidites were studied as synthons for preparing natural and modified intenucleotide linkages. Of the various aryl derivatives examined, the 3'-O-phenylphosphoramidite was found to be the most attractive. It reacted with high overall yield to form deoxydinucleoside O-phenylphosphite triesters which were converted to phosphoramidates, methylphosphonates, and H-phosphonates.

Exact definition of species-specific and cross-reactive epitopes of the 65-kilodalton protein of Mycobacterium leprae using synthetic peptides.

With the use of solid phase synthesis of peptides corresponding to major and minor peaks in a Hopp-Woods hydrophilicity plot, the epitopes for 10 of 14 known different mAb to the Mycobacterium leprae 65-kDa protein, a prominent T and B cell Ag of this bacillus, have been located in the primary structure. Five epitopes have been precisely mapped by using the synthetic peptides in inhibition ELISA experiments, and five others have been located on peptides of 22 amino acids or less in length. The epitope of an important species-specific antibody, IIIE9, which may be useful for seriodiagnosis of leprosy, appears to be distinguished from the epitope of the antibody IVD2, widely cross-reactive among mycobacteria, not by its sequence, but only by its critical residues. All epitopes studied appear continuous insofar as can be determined by this approach.

A New 5′-Protecting Group for Use in Solid-Phase Synthesis of Oligoribonucleotides

Abstract The 2-(2,4-dinitrobenzenesulphenyloxymethyl)benzoyl (DNBSB) group is proposed as a protecting group for the 5′-position of nucleosides. The DNBSB group may be removed under mild non-acidic conditions and may have potential in solid-phase synthesis of oligoribo- and oligodeoxyribonucleotides.