First synthesis of segetalin A and analogous cyclohexapeptides

Authors
Sonnet, P Petit, L Marty, D Guillon, J Rochette, J Brion, JD
Citation
P. Sonnet et al., First synthesis of segetalin A and analogous cyclohexapeptides, TETRAHEDR L, 42(9), 2001, pp. 1681-1683
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1681 - 1683
Database
ISI
SICI code
0040-4039(20010226)42:9<1681:FSOSAA>2.0.ZU;2-B
Abstract
The first synthesis of segetalin A and two analogues is described. Peptide cyclisation was carried out between L-glycine and L-alanine residues in the linear hexapeptide at the final step of the synthesis. Diphenylphosphoryl azide (DPPA) gave the best results as a coupling reagent without epimerisat ion. The synthesized segetalin A was completely identical to the natural co mpound with respect to its physicochemical properties. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.