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Mar. Drugs 2015, 13(12), 7285-7300; doi:10.3390/md13127065

Isolation and Synthesis of Laxaphycin B-Type Peptides: A Case Study and Clues to Their Biosynthesis

1
Centre de Recherche Insulaire et Observatoire de l’Environnement (CRIOBE), USR 3278 EPHE-CNRS-UPVD, Université de Perpignan Via Domitia, 58 avenue P. Alduy, 66860 Perpignan, France
2
Centre de Recherche Insulaire et Observatoire de l’Environnement (CRIOBE), USR 3278 EPHE-CNRS-UPVD, BP 1013 Papetoai, Moorea, French Polynesia, France
3
Laboratoire d’Excellence “Corail”, 58, avenue Paul Alduy, 66860 Perpignan, France
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Vassilios Roussis
Received: 15 October 2015 / Accepted: 30 November 2015 / Published: 5 December 2015
(This article belongs to the Special Issue Compounds from Cyanobacteria)
View Full-Text   |   Download PDF [644 KB, uploaded 5 December 2015]   |  

Abstract

The laxaphyci’s B family constitutes a group of five related cyclic lipopeptides isolated from diverse cyanobacteria from all around the world. This group shares a typical structure of 12 amino acids from the l and d series, some of them hydroxylated at the beta position, and all containing a rare beta-amino decanoic acid. Nevertheless, they can be differentiated due to slight variations in the composition of their amino acids, but the configuration of their alpha carbon remains conserved. Here, we provide the synthesis and characterization of new laxaphycin B-type peptides. In doing so we discuss how the synthesis of laxaphycin B and analogues was developed. We also isolate minor acyclic laxaphycins B, which are considered clues to their biosynthesis. View Full-Text
Keywords: non ribosomal peptides; cyclic lipopeptide; solid phase peptide synthesis; Anabaena; Lyngbya non ribosomal peptides; cyclic lipopeptide; solid phase peptide synthesis; Anabaena; Lyngbya
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MDPI and ACS Style

Bornancin, L.; Boyaud, F.; Mahiout, Z.; Bonnard, I.; Mills, S.C.; Banaigs, B.; Inguimbert, N. Isolation and Synthesis of Laxaphycin B-Type Peptides: A Case Study and Clues to Their Biosynthesis. Mar. Drugs 2015, 13, 7285-7300.

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