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

Marine Drugs

Louis Bornancin²  France Boyaud²  Zahia Mahiout²  Isabelle Bonnard²  Suzanne C. Mills¹  Bernard Banaigs²  Nicolas Inguimbert² 

[1] Centre de Recherche Insulaire et Observatoire de l’Environnement (CRIOBE), USR 3278 EPHE-CNRS-UPVD, BP 1013 Papetoai, Moorea, French Polynesia, France;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;

关键词: non ribosomal peptides;    cyclic lipopeptide;    solid phase peptide synthesis;    Anabaena;    Lyngbya;   

DOI  :  10.3390/md13127065

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.