22728-88-7

Basic information

• Product Name: L-Cysteine, S-(phenylmethyl)-, methyl ester
• CAS NO: 22728-88-7
• Molecular Formula: C11H15NO2S
• Molecular Weight: 225.312
• Mol File: 22728-88-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: L-Cysteine, S-(phenylmethyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine, S-(phenylmethyl)-, methyl ester(22728-88-7)
• EPA Substance Registry System: L-Cysteine, S-(phenylmethyl)-, methyl ester(22728-88-7)

Safety Data

• Hazardous Substances Data: 22728-88-7(Hazardous Substances Data)

Upstream product

• 3054-01-1 S-benzyl-L-cysteine 
• 1243655-37-9 N-nosyl-L-cysteine(SBn) methyl ester 
• 100-39-0 benzyl bromide 
• 67-56-1 methanol 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 100-44-7 benzyl chloride 
• 16741-80-3 S-benzyl-L-cysteine methyl ester hydrochloride 

Downstream Products

• 16869-66-2 S-benzyl-N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-cysteine methyl ester 
• 20987-51-3 S-benzyl-N-(N²-benzyloxycarbonyl-L-asparaginyl)-L-cysteine methyl ester 
• 101033-77-6 S-benzyl-N-((S)-2-benzyloxycarbonylamino-3-cyano-propionyl)-L-cysteine methyl ester 
• 102760-02-1 S-benzyl-N-(S-benzyl-N-formyl-L-cysteinyl)-L-cysteine methyl ester 
• 116032-96-3 S-benzyl-N-[N-(toluene-4-sulfonyl)-L-pyroglutamyl]-L-cysteine-methyl ester 
• 953-18-4 S-benzyl-L-cysteine ethyl ester 
• 70707-56-1 Boc-Thr(CH₂Ph)-Cys(CH₂Ph)-OMe 
• 104979-31-9 N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert-butylester)-S-benzyl-cystein-methylester 
• 105002-40-2 N-(N-Tosyl-L-γ-glutamyl-1-tert.-butylester)-S-benzyl-L-cystein-methylester 
• 106506-91-6 N^α-Benzyloxycarbonyl-N^ω-nitro-L-arginyl-S-benzyl-L-cystein-methylester 
• 16359-97-0 L-S-benzylcysteine amide 
• 15353-95-4 Ac-L-Cys(Bzl)-NHMe 
• 98688-00-7 N-(t-butoxycarbonyl)-L-alanyl-S-benzyl-L-cysteine methyl ester 
• 19261-06-4 4-hydroxydibenzofuran 

Relevant articles and documents

Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam3CSK4-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 ± 2.60 μM. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam3CSK4 triggered TNF-α cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam3CSK4 ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-α, to realize its anti-inflammatory activity.

Deprotection/reprotection of the amino group in α-amino acids and peptides. A one-pot procedure in [Bmim][BF4] ionic liquid

This paper presents an efficient one-pot protocol for the sequential deprotection/reprotection of the α-amino group in α-amino acid and dipeptide methyl esters. [Bmim][BF4] is used as the solvent in the entire process. In particular, the use of the ionic liquid allows for rapid and clean removal of the 4-nitrobenzenesulfonyl (nosyl) group and for facile subsequent tert-butyloxycarbonylation of the free α-amino function under very mild conditions. N-Boc-α-amino acid as well as peptide derivatives are isolated in excellent yields, and do not require any further purification. Absolute configurations of the precursors are totally preserved during the process.

SYNTHESIS OF ETHYL N-CARBOBENZOXYTYROSYL-S-BENZYLCYSTEINYLGLYCINATE

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