34804-98-3

Basic information

• Product Name: L-Cysteine, N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, methyl ester
• CAS NO: 34804-98-3
• Molecular Formula: C15H20N2O5S
• Molecular Weight: 340.4
• Mol File: 34804-98-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Cysteine, N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine, N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, methyl ester(34804-98-3)
• EPA Substance Registry System: L-Cysteine, N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, methyl ester(34804-98-3)

Safety Data

• Hazardous Substances Data: 34804-98-3(Hazardous Substances Data)

Upstream product

• 77834-03-8 methyl S-<<2-<(benzyloxycarbonyl)-L-alanyloxy>phenyl>thio>-L-cysteinate 
• 77834-01-6 (R)-2-Amino-3-[2-((S)-2-benzyloxycarbonylamino-propionyloxy)-5-chloro-benzyldisulfanyl]-propionic acid methyl ester 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 35101-42-9 N-Benzyloxycarbonyl-L-alanyl-S-chlorocarbonyl-L-cystein-methylester 
• 58202-80-5 2-<(S)-1-benzyloxycarbonylaminoethyl>-4-carbomethoxy-(R)-Δ2-thiazoline 
• 34804-99-4 N-Benzyloxycarbonyl-L-alanyl-S-(N-phenylcarbamoyl)-L-cystein-methylester 
• 1244028-34-9 C₁₅H₁₉N₃O₆S 
• 1382089-60-2 C₂₂H₂₃N₃O₅S₂ 
• 1262406-62-1 C₂₂H₂₃N₃O₅S₃ 

Relevant articles and documents

Rational Design of Templates for Intramolecular O,N-Acyl Transfer via Medium-Sized Cyclic Intermediates Derived from L-Cysteine. Definition of an Experimental Maximum in Effective Molarity through the Study of "Tunable" Templates

Rate constants and effective molarities for intramolecular O,N-acyl transfer have been measured for a series of unsymmetrical disulfides derived from cysteine and having the general structure H-Cys(S-XY-OAc)-OMe, for which XY is a rigid molecular spacing element that maintains a fixed OS distance lying in the range of 4.5-6.5 Angstroem.A synthetic route is described to 4-hydroxy-6-mercaptodibenzothiophene, involving lithiation of 4-methoxydibenzothiophene followed by reaction with elemental sulfur and positional isomer separation.A maximum effective molarity (EM) value of 5 M is seen for 4,6-disubstituted dibenzofuran function (OS = 5.45 Angstroem) while EM values of less than 0.1 M are seen for 4,6-disubstituted phenoxathiin and 4,6-disubstituted dibenzothiophene functions (OS = 3.90 and 6.30 Angstroem, respectively).Distance calculations and estimates of strain energy based on torsional and van der Waals terms are used to show that this result is consistent with a cyclic transition state containing one conformation of the cysteine framework.Energy minimization calculations were carried out by using a novel null-vector procedure for finding allowed torsional motions.They imply that the transition state for O,N-acyl transfer is strained by ca. 6 kcal/mol in the dibenzofuran case.

MODELS THAT DEMONSTRATE PEPTIDE BOND FORMATION BY PRIOR THIOL CAPTURE I. CAPTURE BY DISULFIDE FORMATION

Unsymmetrical disulfides formed from L-cysteine esters and o-Cbz-L-alaninyloxybenzenethiol 9, 2-Cbz-L-alaninyloxy-5-chlorophenylmethylenethiol 8, 4-acetoxyxanthenylmethylenethiol 10, and 1,5-diacetoxy-2-methyl-3-methoxy-4-thioxanthone 11 are observed to undergo intramolecular O,N-acyl transfer in yields up to 60percent, with accompanying disulfide interchange.The significance of these results for a general amide forming strategy of prior cysteine capture are discussed.