77549-14-5

Basic information

• Product Name: N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER
• Synonyms: N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER;N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER 99%;N-Acetyl-S-benzyl-L-cysteine methyl ester,99%
• CAS NO: 77549-14-5
• Molecular Formula: C₁₃H₁₇NO₃S
• Molecular Weight: 267.34
• Product Categories: Amino Acids
• Mol File: 77549-14-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 67-73 °C
• Boiling Point: 451.4oC at 760 mmHg
• Flash Point: 226.8oC
• Appearance: /
• Density: 1.2230 (rough estimate)
• Vapor Pressure: 2.43E-08mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER(77549-14-5)
• EPA Substance Registry System: N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER(77549-14-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 77549-14-5(Hazardous Substances Data)

Usage

Chemical Properties

WHITE FINE CRYSTALLINE POWDER

InChI:InChI=1/C13H17NO3S/c1-10(15)14-12(13(16)17-2)9-18-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,15)/t12-/m0/s1

Upstream product

• 22728-88-7 S-benzylcysteine methyl ester 
• 101762-41-8 4-acetoxyphenoxathiin 
• 100-53-8 phenylmethanethiol 
• 151910-16-6 methyl (2S)-(-)-1-acetylaziridine-2-carboxylate 
• 101762-27-0 4-acetoxydibenzofuran 
• 67-56-1 methanol 
• 19538-71-7 N-acetyl-S-benzyl-D,L-cysteine 

Relevant articles and documents

Templates for Intramolecular O,N-Acyl Transfer via Cyclic Intermediates Derived from Mercury Derivatives of L-Cysteine: Progress toward a Mercury-Based Thiol Capture Strategy

A first study is reported of optimization of a template bridging an oxygen ester with mercury that facilitates intramolecular O,N-acyl transfer from a phenolic oxygen to the amino group of a cysteine residue that is functionalized at sulfur as an arylmercuri complex.Respective effective molarities (EM values) of 0.28, ca. 0.6, and 0.0 are observed for the following three arylmercuri complexes: methyl S-((4-acetoxy-6-phenoxathiinyl)mercuri)-L-cysteinate (9), methyl S-((5-acetoxy-1,3-dimethoxy-2-methyl-9-oxoxanth-4-yl)mercuri)-L-cysteinate (10), and methyl S-((4-acetoxydibenzofuran-6-yl)mercuri)-L-cysteinate (11).Syntheses of these compounds are reported, and the structural significance of the EM values for transition states of the acyl-transfer reactions is discussed.The observed reactivity pattern is consistent with a linear geometry at the mercury atom and a geometry about the forming C-N bond of other than the trans, anti relationship that has been observed for intermolecular acyl-transfer reactions.

Peptide Synthesis by Prior Thiol Capture. 2. Design of Templates for Intramolecular O,N-Acyl Transfer. 4,6-Disubstituted Dibenzofurans as Optimal Spacing Elements

A central feature of the strategy for amide bond formation by prior thiol capture is an intramolecular acyl transfer across a template that links the phenolic ester function of one peptide with an unsymmetrical disulfide involving the side chain of the N-terminal cysteine residue of a second peptide.The structures of the 4-hydroxy-6-mercaptodibenzofuran (3) and 4-hydroxy-6-mercaptophenoxythiin (4) are established by 1H NMR spectra of deuterated dibenzofuran and phenoxythiin derivatives.On the basis of the criterion of effective molarity, a dibenzofuran template for intramolecular acyl transfer is shown to be approximately 2 orders of magnitude more efficient than a phenoxythiin.An effective local concentration of ca. 5 M and a Hammett ρ value of 2.6 are observed for the intramolecular acyl-transfer reaction 1 -> 2.