98854-91-2

Basic information

• Product Name: Z-D-a-vinyl-Gly-OMe
• Synonyms: Z-D-a-vinyl-Gly-OMe;Z-D-α-vinyl-Gly-OMe;(R)-METHYL 2-(((BENZYLOXY)CARBONYL)AMINO)BUT-3-ENOATE
• CAS NO: 98854-91-2
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.2625
• Mol File: 98854-91-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Z-D-a-vinyl-Gly-OMe(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-a-vinyl-Gly-OMe(98854-91-2)
• EPA Substance Registry System: Z-D-a-vinyl-Gly-OMe(98854-91-2)

Safety Data

• Hazardous Substances Data: 98854-91-2(Hazardous Substances Data)

Usage

General Description

Z-D-a-vinyl-Gly-OMe is a chemical compound used in the field of peptide chemistry as a protecting group for the amino acid glycine. The Z-D-a-vinyl-Gly-OMe molecule acts as a temporary shield for the glycine residue during peptide synthesis, protecting it from unwanted reactions with other reagents. This protection allows for the selective modification of other amino acid residues in the peptide chain. The Z-D-a-vinyl-Gly-OMe group can be removed under mild conditions after the desired modifications have been made, leaving the glycine residue intact and allowing for the synthesis of complex and specifically modified peptides.

Upstream product

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

Downstream Products

• 128134-29-2 2-((R)-Benzyloxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid ethyl ester 
• 111581-53-4 (S)-2-Benzyloxycarbonylamino-3-chloro-4-phenylselanyl-butyric acid methyl ester 
• 98777-29-8 methyl (2R,3R)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate 
• 91103-38-7 (R)-(1-hydroxymethallyl)carbamic acid benzyl ester 
• 52795-52-5 D-vinylglycine 
• 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 

Relevant articles and documents

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.

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.