Literature DB >> 23855751

First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A.

France Boyaud1, Zahia Mahiout, Christine Lenoir, Shoubin Tang, Joanna Wdzieczak-Bakala, Anne Witczak, Isabelle Bonnard, Bernard Banaigs, Tao Ye, Nicolas Inguimbert.   

Abstract

The first total synthesis of laxaphycin B was accomplished through stepwise automated Solid Phase Peptide Synthesis (SPPS), leading to the structural revision of its stereochemistry especially with regard to the configuration of one of the two 3-hydroxyleucines of this cyclic dodecapeptide of marine origin. The analogous Lyngbyacyclamide A was obtained by an extension of this synthesis.

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Year:  2013        PMID： 23855751     DOI： 10.1021/ol401645m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045.

Authors:  Shangwen Luo; Hahk-Soo Kang; Aleksej Krunic; Wei-Lun Chen; Jilai Yang; John L Woodard; James R Fuchs; Sang Hyun Cho; Scott G Franzblau; Steven M Swanson; Jimmy Orjala
Journal:  Bioorg Med Chem       Date:  2015-05-01       Impact factor: 3.641

Review 2.  Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

Authors:  Vedanjali Gogineni; Mark T Hamann
Journal:  Biochim Biophys Acta Gen Subj       Date:  2017-08-24       Impact factor: 3.770

3.  Discovery of new A- and B-type laxaphycins with synergistic anticancer activity.

Authors:  Weijing Cai; Susan Matthew; Qi-Yin Chen; Valerie J Paul; Hendrik Luesch
Journal:  Bioorg Med Chem       Date:  2018-03-14       Impact factor: 3.641

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

Authors:  Louis Bornancin; France Boyaud; Zahia Mahiout; Isabelle Bonnard; Suzanne C Mills; Bernard Banaigs; Nicolas Inguimbert
Journal:  Mar Drugs       Date:  2015-12-05       Impact factor: 5.118

Review 5.  New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade.

Authors:  Yue Mi; Jinrong Zhang; Shan He; Xiaojun Yan
Journal:  Mar Drugs       Date:  2017-05-05       Impact factor: 5.118

6.  Epoxinnamide: An Epoxy Cinnamoyl-Containing Nonribosomal Peptide from an Intertidal Mudflat-Derived Streptomyces sp.

Authors:  Sangwook Kang; Jaeho Han; Sung Chul Jang; Joon Soo An; Ilnam Kang; Yun Kwon; Sang-Jip Nam; Sang Hee Shim; Jang-Cheon Cho; Sang Kook Lee; Dong-Chan Oh
Journal:  Mar Drugs       Date:  2022-07-12       Impact factor: 6.085

7.  Biophysical Studies of the Induced Dimerization of Human VEGF Receptor 1 Binding Domain by Divalent Metals Competing with VEGF-A.

Authors:  Jean-François Gaucher; Marie Reille-Seroussi; Nathalie Gagey-Eilstein; Sylvain Broussy; Pascale Coric; Bili Seijo; Marie-Bernard Lascombe; Benoit Gautier; Wang-Quing Liu; Florent Huguenot; Nicolas Inguimbert; Serge Bouaziz; Michel Vidal; Isabelle Broutin
Journal:  PLoS One       Date:  2016-12-12       Impact factor: 3.240

8.  Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells.

Authors:  Rebeca Alvariño; Eva Alonso; Louis Bornancin; Isabelle Bonnard; Nicolas Inguimbert; Bernard Banaigs; Luis M Botana
Journal:  Mar Drugs       Date:  2020-07-15       Impact factor: 5.118

Review 9.  Thirtieth Anniversary of the Discovery of Laxaphycins. Intriguing Peptides Keeping a Part of Their Mystery.

Authors:  Laurine Darcel; Sanjit Das; Isabelle Bonnard; Bernard Banaigs; Nicolas Inguimbert
Journal:  Mar Drugs       Date:  2021-08-24       Impact factor: 5.118
  9 in total

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