2577-41-5

Basic information

• Product Name: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, phenylmethyl ester
• CAS NO: 2577-41-5
• Molecular Formula: C33H32N2O5
• Molecular Weight: 536.627
• Mol File: 2577-41-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, phenylmethyl ester(2577-41-5)
• EPA Substance Registry System: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, phenylmethyl ester(2577-41-5)

Safety Data

• Hazardous Substances Data: 2577-41-5(Hazardous Substances Data)

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 63-91-2 L-phenylalanine 
• 13122-91-3 N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanine 
• 100-39-0 benzyl bromide 
• 962-39-0 L-Phenylalanine benzyl ester 

Relevant articles and documents

Catalytic dehydrative peptide synthesis with gem-diboronic acids

Alkane-gem-diboronic acids have emerged as versatile organoboron catalysts for dehydrative amidation of α-Amino acids. A phenol-substituted multiboron catalyst with a B-C-B structure outperformed simple arylboronic acids in the condensation of α-Amino acids with suppressed epimerization of electrophiles. gem-diboronic acid catalysis were compatible with various O, N, and S-functionalized α-Amino acids bearing N-protecting groups including common carbamates used in peptide synthesis (Boc, Cbz, Fmoc). N-Trifluoroacetyl protection enabled an unprecedented catalytic dehydrative peptide synthesis at room temperature. Preliminary mechanistic studies revealed carboxylate-binding nature of gem-diboronic acids, orthogonal to the activation of carboxylic acids by arylboronic acids. The distinctive reactivity of the gem-diboronic acids would open prospects for mild catalytic peptide condensation.

Immunomodulators

The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

ENZYMIC SYNTHESIS OF OLIGOPETIDE - VI. THE MECHANISTIC FEATURES OF PEPSIN-CATALYSED PEPTIDE SYNTHESIS

The dipeptide Z-Phe-Phe-OBzl and tripeptide Z-Phe-Phe-Phe-OBzl were synthesized by pepsin catalysis from the incubation of Z-Phe and Phe-OBzl in the reaction solution.The yield ratio of two peptides in relation to reaction time was investigated by HPLC.Another example: The tripeptide Z-Phe-Leu-Phe-OBzl and tetrapeptide Z-Phe-Leu-Phe-Phe-OBzl were also synthesized concurrently from Z-Phe-Leu and Phe-OBzl by pepsin catalysis.These results may have important implication for the transpeptidation of pepsin.But, according to the report of Pellegrini and Luisi, the dipeptide, Z-Ph-Phe-OBzl, synthesized by pepsin catalysis was not contaminated with the tripeptide,Z-Phe-Phe-Phe-OBzl, and the yield was high.In order to investigate the discrepancies between our observation and those reported by Pellegrini and Luisi, a mechanism by which pepsin synthesizes the dipeptide, Z-Phe-Phe-OBzl, and tripeptide, Z-Phe-Phe-Phe-OBzl, is proposed and supporting data demonstrated by HPLC analysis.