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

• Published in: Marine drugs Vol. 13; no. 12; pp. 7285 - 7300
• Main Authors: Bornancin, Louis, Boyaud, France, Mahiout, Zahia, Bonnard, Isabelle, Mills, Suzanne C, Banaigs, Bernard, Inguimbert, Nicolas
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI 05.12.2015; MDPI AG
• Subjects: Amino Acid Sequence; Anabaena; Cyanobacteria - chemistry; Cyanobacteria - metabolism; cyclic lipopeptide; Lyngbya; non ribosomal peptides; Peptides, Cyclic - biosynthesis; Peptides, Cyclic - isolation & purification; solid phase peptide synthesis; non ribosomal peptides; solid phase peptide synthesis; cyclic lipopeptide; Lyngbya; Anabaena
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md13127065

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.