312328-55-5

Basic information

• Product Name: (S)-Alloc-Dhpg(OBn)2-OH
• Synonyms: (S)-Alloc-Dhpg(OBn)2-OH
• CAS NO: 312328-55-5
• Molecular Weight: 447.488
• Mol File: 312328-55-5.mol

Chemical Properties

• CAS DataBase Reference: (S)-Alloc-Dhpg(OBn)2-OH(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Alloc-Dhpg(OBn)2-OH(312328-55-5)
• EPA Substance Registry System: (S)-Alloc-Dhpg(OBn)2-OH(312328-55-5)

Safety Data

• Hazardous Substances Data: 312328-55-5(Hazardous Substances Data)

Upstream product

• 312328-67-9 (S)-3-[(S)-2-Azido-2-(3,5-bis-benzyloxy-phenyl)-acetyl]-4-benzyl-oxazolidin-2-one 
• 52144-91-9 3,5-bis(benzyloxy)diazoacetophenone 
• 135387-91-6 (S)-4-Benzyl-3-[2-(3,5-bis-benzyloxy-phenyl)-acetyl]-oxazolidin-2-one 
• 100-44-7 benzyl chloride 
• 28917-44-4 3,5-dibenzyloxylbenzoyl chloride 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 
• 2732-96-9 3,5-dibenzyloxyphenylacetic acid 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 312328-68-0 [(S)-2-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-1-(3,5-bis-benzyloxy-phenyl)-2-oxo-ethyl]-carbamic acid allyl ester 

Downstream Products

• 851968-86-0 (S)-Allyloxycarbonylamino-(3,5-dihydroxy-phenyl)-acetic acid 

Relevant articles and documents

An improved solid-phase methodology for the synthesis of putative hexa- and heptapeptide intermediates in vancomycin biosynthesis

The biosynthesis of the vancomycin aglycone involves three oxidative phenol coupling reactions, each catalyzed by a discrete cytochrome P450-like enzyme. Studies on the mechanism and specificity of the enzyme (called OxyB) catalyzing the first coupling, require access to suitable linear peptide precursors, each conjugated as a thioester to a peptide carrier domain of the vancomycin non-ribosomal peptide synthetase. An efficient route to representative free linear peptides is described here. The method makes use of Alloc-chemistry during solid-phase assembly of the peptide backbone, but importantly and in contrast to earlier efforts, largely avoids the use of amino acid side chain protecting groups. In this way, the target linear peptides can be released directly from the solid support under very mild conditions. The Royal Society of Chemistry 2005.

Solid-phase synthesis using (Allyloxy)carbonyl(Alloc) chemistry of a putative heptapeptide intermediate in vancomycin biosynthesis containing m-chloro-3-hydroxytyrosine

A convenient method for the solid-phase synthesis of putative linear heptapeptide intermediates in vancomycin biosynthesis is described, in particular, the heptapeptide D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt = (2R,3R)-m-chloro-3-hydroxytyrosine, Hpg = (R)-2-(p-hydroxyphenyl)glycine, Cyt' = (2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg = (S)-2-(3,5-dihydroxyphenyl)glycine). The synthesis was performed on chlorotrityl resin and employed the (allyloxy)carbonyl protecting group for temporary N(α) protection during peptide-chain assembly.