A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey–Nicolaou) resulted in significant epimerization of the C-terminal amino acid during t...

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Autores principales: Cochrane, James R, Yoon, Dong Hee, McErlean, Christopher S P, Jolliffe, Katrina A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458759/
https://www.ncbi.nlm.nih.gov/pubmed/23019469
http://dx.doi.org/10.3762/bjoc.8.154
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author Cochrane, James R
Yoon, Dong Hee
McErlean, Christopher S P
Jolliffe, Katrina A
author_facet Cochrane, James R
Yoon, Dong Hee
McErlean, Christopher S P
Jolliffe, Katrina A
author_sort Cochrane, James R
collection PubMed
description The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey–Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.
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spelling pubmed-34587592012-09-27 A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues Cochrane, James R Yoon, Dong Hee McErlean, Christopher S P Jolliffe, Katrina A Beilstein J Org Chem Full Research Paper The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey–Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product. Beilstein-Institut 2012-08-21 /pmc/articles/PMC3458759/ /pubmed/23019469 http://dx.doi.org/10.3762/bjoc.8.154 Text en Copyright © 2012, Cochrane et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Cochrane, James R
Yoon, Dong Hee
McErlean, Christopher S P
Jolliffe, Katrina A
A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title_full A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title_fullStr A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title_full_unstemmed A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title_short A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
title_sort macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide li-f04a and diastereoisomeric analogues
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458759/
https://www.ncbi.nlm.nih.gov/pubmed/23019469
http://dx.doi.org/10.3762/bjoc.8.154
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