Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation

Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formatio...

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Autores principales: Fuse, Shinichiro, Mifune, Yuto, Nakamura, Hiroyuki, Tanaka, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5133696/
https://www.ncbi.nlm.nih.gov/pubmed/27892469
http://dx.doi.org/10.1038/ncomms13491
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author Fuse, Shinichiro
Mifune, Yuto
Nakamura, Hiroyuki
Tanaka, Hiroshi
author_facet Fuse, Shinichiro
Mifune, Yuto
Nakamura, Hiroyuki
Tanaka, Hiroshi
author_sort Fuse, Shinichiro
collection PubMed
description Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically active oligopeptides that contain highly racemizable amino acids, which are attractive drug candidates.
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spelling pubmed-51336962016-12-21 Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation Fuse, Shinichiro Mifune, Yuto Nakamura, Hiroyuki Tanaka, Hiroshi Nat Commun Article Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically active oligopeptides that contain highly racemizable amino acids, which are attractive drug candidates. Nature Publishing Group 2016-11-28 /pmc/articles/PMC5133696/ /pubmed/27892469 http://dx.doi.org/10.1038/ncomms13491 Text en Copyright © 2016, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Fuse, Shinichiro
Mifune, Yuto
Nakamura, Hiroyuki
Tanaka, Hiroshi
Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title_full Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title_fullStr Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title_full_unstemmed Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title_short Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
title_sort total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5133696/
https://www.ncbi.nlm.nih.gov/pubmed/27892469
http://dx.doi.org/10.1038/ncomms13491
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