183609-76-9

Upstream product

• 183609-98-5 (R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 183609-55-4 L-phenylalanyl-D-proline methyl ester 
• 4892-10-8 N-(benzyloxycarbonyl)-L-phenylalanyl-L-phenylalanine methyl ester 
• 13122-91-3 N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanine 

Downstream Products

• 197631-11-1 C₃₆H₄₇⁽³⁾HN₄O₇ 
• 183609-81-6 (5S,8S,11S,13aR)-5,8-Dibenzyl-11-[5-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentyl]-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 
• 183609-99-6 (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 183610-00-6 Toluene-4-sulfonic acid (4S,5S)-5-[5-((5S,8S,11S,13aR)-5,8-dibenzyl-4,7,10,13-tetraoxo-tetradecahydro-3a,6,9,12-tetraaza-cyclopentacyclododecen-11-yl)-pentyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 

Relevant academic research and scientific papers

A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization

A modular synthesis of some cyclic peptides related to a class of histone deacetylase inhibitors is reported. The synthesis utilizes a late-stage functionalization of a cyclic tetrapeptide scaffold to link the pendant alkyl chain through cross metathesis. It is observed that while the cross-metathesis reaction of a terminal olefin having a β-substituent is marginally successful with the scaffold, the corresponding reaction with an α,β-unsaturated ketone/ester is more promising. The utility of the protocol is demonstrated through the preparation of three cyclic tetrapeptides structurally related to the novel histone deacetylase inhibitors FR-225497 and trapoxin B.

Synthesis of natural and modified trapoxins, useful reagents for exploring histone deacetylase function

Trapoxin, a cyclotetrapeptide isolated from the fungus Helicoma ambiens, profoundly affects mammalian cell growth and morphology. In this paper, we describe syntheses of trapoxin, [3H]trapoxin, and K-trap, a trapoxin-based affinity reagent. The