153723-34-3

Usage

InChI:InChI=1/C39H58N8O8/c1-21(2)18-26-38(54)47-17-11-15-29(47)35(51)45-32(23(5)6)37(53)43-27(20-30(40)48)39(55)46-16-10-14-28(46)34(50)41-25(19-24-12-8-7-9-13-24)33(49)44-31(22(3)4)36(52)42-26/h7-9,12-13,21-23,25-29,31-32H,10-11,14-20H2,1-6H3,(H2,40,48)(H,41,50)(H,42,52)(H,43,53)(H,44,49)(H,45,51)/t25-,26-,27-,28-,29?,31+,32-/m0/s1

Upstream product

• 71989-31-6 Fmoc-Pro-OH 
• 184589-19-3 N-Fmoc-L-Val-L-Asn-L-Pro-L-Phe-L-Val-L-Leu-L-Pro-O-(t-Bu) 
• 184589-18-2 (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-17-1 N-Fmoc-L-Pro-L-Phe-L-Val-L-Leu-L-Pro-O-(t-Bu) 
• 184589-38-6 (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-carbamoyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-37-5 (S)-1-{(S)-2-[(S)-2-((S)-2-{[(S)-1-((S)-2-Amino-3-carbamoyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-propionylamino)-3-methyl-butyrylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-16-0 (S)-1-((S)-2-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-36-4 (S)-1-[(S)-4-Methyl-2-((S)-3-methyl-2-{(S)-3-phenyl-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionylamino}-butyrylamino)-pentanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-15-9 (S)-1-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-35-3 (S)-1-{(S)-2-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-methyl-butyrylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 184589-14-8 Fluorenylmethoxycarbonylleucyl-proline tert-butyl ester 
• 129472-19-1 (9H-fluoren-9-yl)methyl tert-butylpyrrolidine-1,2-dicarboxylate 
• 184589-34-2 (S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 74509-15-2 leucylproline tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of axinastatins 2-5

The cytotoxic cyclic peptides axinastatin 2, 3, 4 and 5, isolated from the ocean marine sponges Axinella sp. and Axinella cf. cateri, were synthesized and characterized by FAB-MS and homo- and heteronuclear NMR spectroscopy. The synthetic compounds proved to be identical with the natural products. The cyclization yield of axinastatin 5 could be increased using structural information of a conformationally comparable compound. In contrast to the published biological activity very low activities were found for all compounds.

Synthesis of the cyclic heptapeptides Axinastatin 2 and Axinastatin 3

Practical total syntheses of axinastatins 2 2b and 3 2c were completed by employing Fmoc protection for the N-terminal, and tert-butyl ester blocking for the C-terminal, units of the amlno add and peptide intermediates. Generally, diethyl phosphorocyanidate proved effective for formation of the peptide bond, and in the one exception, asparagine, the o-nitrophenyl active ester proved to be useful. For the final cyclization reaction BOP-Cl was found especially effective. Copyright 1996 by the Royal Society of Chemistry.