171813-89-1

Basic information

• Product Name: L-Tyrosine, N-acetyl-O-2-propenyl-
• CAS NO: 171813-89-1
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• Mol File: 171813-89-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: L-Tyrosine, N-acetyl-O-2-propenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tyrosine, N-acetyl-O-2-propenyl-(171813-89-1)
• EPA Substance Registry System: L-Tyrosine, N-acetyl-O-2-propenyl-(171813-89-1)

Safety Data

• Hazardous Substances Data: 171813-89-1(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 107-18-6 allyl alcohol 
• 840-97-1 N-acetyl-L-tyrosine ethyl ester 
• 127132-48-3 ethyl (2S)-2-acetamido-3-(4-allyloxyphenyl)propanoate 
• 127132-38-1 N-(tert-butyloxycarbonyl)-O-allyl-(S)-tyrosine 

Downstream Products

• 484024-16-0 methyl (2S,5S,8S)-2-allyl-8-(4-allyloxybenzyl)-3,6,9-triaza-5-[4-(tert-butoxycarbonyl)aminobutyl]-4,7,10-trioxoundecanoate 
• 484024-20-6 methyl (2S,5S,8S)-2-allyl-8-(4-allyloxybenzyl)-3,6,9-triaza-5-[4-(N,N-di-tert-butoxycarbonyl)guanidinobutyl]-4,7,10-trioxoundecanoate 

Relevant articles and documents

A method for selective N-Boc deprotection on Wang resin

A simple, inexpensive and efficient method for the selective cleavage of N-Boc protecting group under acidic conditions on high load Wang resin is described. This method employs the use of concd sulfuric acid in 1,4-dioxan and provides an efficient process for the complete Boc deprotection with minimal loss of substrate through cleavage from resin.

The discovery of allyltyrosine based tripeptides as selective inhibitors of the HIV-1 integrase strand-transfer reaction

From library screening of synthetic antimicrobial peptides, an O-allyltyrosine-based tripeptide was identified to possess inhibitory activity against HIV-1 integrase (IN) exhibiting an IC50 value of 17.5 μM in a combination 3′-processing and strand transfer microtitre plate assay. The tripeptide was subjected to structure-activity relationship (SAR) studies with 28 peptides, incorporating an array of natural and non-natural amino acids. Resulting SAR analysis revealed the allyltyrosine residue was a key feature for IN inhibitory activity whilst incorporation of a lysine residue and extended hydrophilic chains bearing a terminal methyl ester was advantageous. Addition of hydrophobic aromatic moieties to the N-terminal of the scaffold afforded compounds with improved inhibitory activity. Consolidation of these functionalities lead to the development of the tripeptide 96 which specifically inhibited the IN strand-transfer reaction with an IC50 value of 2.5 μM.

PEPTIDIC COMPOUNDS

The present invention provides a compound of formula (I), (II), (III) and (IV) as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.