17790-88-4

Basic information

• Product Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-phenylhydrazide
• CAS NO: 17790-88-4
• Molecular Formula: C20H25N3O3
• Molecular Weight: 355.437
• Mol File: 17790-88-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-phenylhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-phenylhydrazide(17790-88-4)
• EPA Substance Registry System: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-phenylhydrazide(17790-88-4)

Safety Data

• Hazardous Substances Data: 17790-88-4(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 25616-33-5 2-((2S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)acetic acid 

Downstream Products

• 474316-97-7 Boc-Phe-Phe-NHNHPh 
• 13122-90-2 Boc-Phe-Phe-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Relevant articles and documents

Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis

The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.

Peptide synthesis via oxidation of N-acyl-alpha-amino acid phenylhydrazides. 3. Dialanyl-insulin and diphenylalanyl-insulin.

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