16856-21-6

Basic information

• Product Name: L-Tryptophan, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester
• CAS NO: 16856-21-6
• Molecular Formula: C29H29N3O5
• Molecular Weight: 499.566
• Mol File: 16856-21-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Tryptophan, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tryptophan, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(16856-21-6)
• EPA Substance Registry System: L-Tryptophan, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(16856-21-6)

Safety Data

• Hazardous Substances Data: 16856-21-6(Hazardous Substances Data)

Upstream product

• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 4299-70-1 L-tryptophan methyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 3588-57-6 Z-DL-Phe-OH 

Downstream Products

• 108787-56-0 L-phenylalanyl-L-tryptophan methyl ester 
• 109481-44-9 Z-Asn-Phe-Phe-Trp-N₂H₃ 
• 109481-43-8 Z-Asn-Phe-Phe-Trp-OMe 

Relevant articles and documents

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.

A new synthesis of somatostatin and some potential metabolites

-