4816-89-1

Basic information

• Product Name: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, 2-amino-2-oxoethyl ester
• CAS NO: 4816-89-1
• Molecular Formula: C19H20N2O5
• Molecular Weight: 356.378
• Mol File: 4816-89-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, 2-amino-2-oxoethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, 2-amino-2-oxoethyl ester(4816-89-1)
• EPA Substance Registry System: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, 2-amino-2-oxoethyl ester(4816-89-1)

Safety Data

• Hazardous Substances Data: 4816-89-1(Hazardous Substances Data)

Upstream product

• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 79-07-2 Chloroacetamide 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 33033-71-5 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoate 
• 1161-13-3 N-Cbz-L-Phe 
• 29842-94-2 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-4-methylpentanoate 
• 28944-94-7 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoate 
• 106556-07-4 Z-Phe-Leu-Ala-NH₂ 
• 17430-32-9 N--(S)-α-methylbenzylamine 
• 141056-54-4 N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalaninamide 
• 71450-10-7 benzyl N-((1S)-2-[(1S)-1-(aminocarbonyl)-3-(methylsulfanyl)propyl]amino-1-benzyl-2-oxoethyl)carbamate 
• 76264-55-6 Z-L-Phe-L-Ser-NH₂ 
• 69193-11-9 Z-L-Phe-L-Val-NH₂ 
• 17187-05-2 Z-L-phenylalanylglycinamide 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 83871-06-1 N-benzyloxycarbonyl-L-phenylalanyl-L-prolinamide 
• 2899-09-4 benzyloxycarbonyl-L-phenylalanyl-L-proline tert-butyl ester 

Relevant articles and documents

Kinetically controlled peptide synthesis mediated by papain using the carbamoylmethyl ester as an acyl donor

A series of dipeptides were synthesized generally in good yields with carbamoylmethyl (Cam) esters as acyl donors in the presence of a cysteine protease, papain, immobilized on Celite. Several segment condensations were also achieved generally in high yields without danger of racemization and formation of the secondary-hydrolysis product. Moreover, partial sequences of some bioactive peptides were prepared through segment condensations, and aimed-at peptides were obtained generally in high yields without the racemization of C-terminal residues of the carboxyl components. Thus, the superiority of the Cam ester in the kinetically controlled peptide synthesis was once again ascertained in couplings mediated by the cysteine protease as in those catalyzed by the serine proteases reported earlier.

On the Use of Carboxamidomethyl Esters in the Protease-Catalyzed Peptide Synthesis

Carboxyamidomethyl esters (CAM esters) of Z-and Boc-protected alanine and phenylalanine were prepared in order to investigate their usefulness as substrates for α-chymotrypsin- and papain-catalyzed hydrolysis and peptide synthesis reactions.The easy removal of the CAM-C-protecting group under mild conditions and dependent on the enzyme specificity was demonstrated.Examples are given for the protease-catalyzed synthesis of various peptide derivatives using CAM esters as C- and N-components in aqueous-organic media.Comparatively short reaction times were observed. - Key words: Carboxyamidomethyl ester as C-protecting group; Enzymatic deprotection; Peptide synthesis; α-Chymotrypsin- and Papain-catalyzed peptide bond formation