98854-91-2

Usage

Uses

Used in Pharmaceutical Industry:
Z-D-a-vinyl-Gly-OMe is used as a protecting group for glycine in the synthesis of complex peptides for various pharmaceutical applications. Its ability to selectively protect glycine residues allows for the precise modification of peptide sequences, leading to the development of more effective and targeted drug candidates.
Used in Biochemical Research:
In biochemical research, Z-D-a-vinyl-Gly-OMe is used as a protecting group for glycine during the synthesis of peptides for studying protein structure, function, and interactions. The selective protection of glycine residues enables researchers to investigate the role of specific amino acids in protein function and develop a deeper understanding of biological processes.
Used in Peptide Synthesis:
Z-D-a-vinyl-Gly-OMe is used as a protecting group for glycine in the synthesis of peptides for various applications, including therapeutics, diagnostics, and research tools. Its ability to selectively protect glycine residues during peptide synthesis allows for the creation of peptides with specific modifications, enhancing their stability, activity, and targeting capabilities.
Used in Chemical Synthesis:
Z-D-a-vinyl-Gly-OMe is used as a protecting group for glycine in the synthesis of complex organic molecules and compounds. Its selective protection of glycine residues enables chemists to incorporate glycine into the molecular structures of various compounds, expanding the scope of chemical synthesis and the development of new materials and reagents.

Upstream product

• 6893-26-1 D-Glutamic acid 
• 80656-34-4 N-<(benzoyloxy)carbonyl>-D,L-vinylglycine methyl ester 
• 501-53-1 benzyl chloroformate 
• 155102-63-9 methyl (2R)-2-(benzyloxycarbonylamino)-4-methylthiobutyrate 
• 21691-49-6 D-methionine methyl ester 

Downstream Products

• 128134-29-2 2-((R)-Benzyloxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid ethyl ester 
• 98777-29-8 methyl (2R,3R)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate 
• 91103-38-7 (R)-(1-hydroxymethallyl)carbamic acid benzyl ester 
• 186759-64-8 (+)-phenylmethyl [(1R)-1-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate 
• 98777-50-5 trans-ethyl (3S,4S)-<3-<<(benzyloxy)carbonyl>amino>-4-hydroxy-(Z)-2-pyrrolidinylidene>acetate 
• 98777-39-0 (2R,3S)-2-<<(benzyloxy)carbonyl>amino>-3-<(tert-butyldimethylsilyl)oxy>-4-azidobutanoic acid 
• 98799-18-9 methyl (2R,3S)-2-<<(benzyloxy)carbonyl>amino>-3-<(tert-butyldimethylsilyl)oxy>-4-azidobutanoate 
• 98777-46-9 ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-hydroxy-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate 
• 98777-45-8 ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-<(tert-butyldimethylsilyl)oxy>-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate 
• 98777-47-0 ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate 
• 98777-37-8 methyl (2R,3S)-4-azido-2-(benzyloxycarbonylamino)-3-hydroxybutanoate 
• 84449-08-1 N-benzyloxycarbamoyl methyl oxamate 
• 111687-20-8 (S)-2-Benzyloxycarbonylamino-3-chloro-but-3-enoic acid methyl ester 
• 111581-54-5 C₁₉H₂₀ClNO₅Se 

Relevant academic research and scientific papers

Crystallographic studies on the reaction of isopenicillin N synthase with an unsaturated substrate analogue

Isopenicillin N synthase (IPNS) catalyses conversion of the linear tripeptie δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (ACV) to isopenicillin N (IPN), the central step in biosynthesis of the β-lactam antibiotics. The unsaturated substrate analogue δ-(L-α-aminoadipoyl)-L-cysteinyl-D-vinylglycine (ACvG) has previously been incubated with IPNS and a single product was isolated, a 2-α-hydroxymethyl isopenicillin N (HMPen), formed via a monooxygenase mode of reactivity. ACvG has now been crystallised with IPNS and the structure of the anaerobic IPNS:Fe(II):ACvG complex determined to 1.15 A resolution. Furthermore, by exposing the anaerobically grown crystals to high-pressure oxygen gas, a structure corresponding to the bicyclic product HMPen has been obtained at 1.60 A resolution. In light of these and other IPNS structures, and recent developments with related dioxygenases, the [2 + 2] cycloaddition mechanism for HMPen formation from ACvG has been revised, and a stepwise radical mechanism is proposed. This revised mechanism remains consistent with the observed stereospecificity of the transformation, but fits better with apparent constraints on the coordination geometry around the active site iron atom.

A flexible synthesis of azasugars and homoazasugars via olefin metathesis

A flexible synthesis of azasugars and homoazasugars from vinyl glycine methyl ester is described. The syntheses, which are based on ring closing olefin metathesis steps and stereocontrolled functionalizations of the formed double bonds, offer a broad vari

D-3,4-'cyclopropylglutamate' isomers as nmda receptor ligands: Synthesis and enantioselective activity

Dirhodium(II) tetraacetate catalyzed decomposition of ethyl diazoacetate in the presence of D-Cbz-vinylglycine methyl ester (11) afforded a mixture of the cyclopropyl esters D-CGA A-D (13) from which the corresponding 2R-acids 7-10 were obtained and their absolute configurations assigned. The (2R,3S,4R) α-(carboxycyclopropyl)glycine (D-CGA C, 9 resulted to be the most potent and selective among the NMDA receptor ligands yet reported.