Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach

Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach

A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisatio...

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Main Authors: Sirirat Kumarn, Nitirat Chimnoi, Somsak Ruchirawat
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Biochemistry, Genetics and Molecular Biology
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/31411
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spelling th-mahidol.314112018-10-19T11:49:49Z Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach Sirirat Kumarn Nitirat Chimnoi Somsak Ruchirawat Mahidol University Chulabhorn Research Institute South Carolina Commission on Higher Education Biochemistry, Genetics and Molecular Biology Chemistry A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisation. It provides access to useful quantities of 1 in 16 steps and 19% overall yield, based on the manufacturer's stated resin substitution from commercially available materials, and also verifies the absolute stereochemistry of the natural product. © The Royal Society of Chemistry 2013. 2018-10-19T04:43:44Z 2018-10-19T04:43:44Z 2013-01-01 Article Organic and Biomolecular Chemistry. Vol.11, No.44 (2013), 7760-7767 10.1039/c3ob41447g 14770520 2-s2.0-84886408136 https://repository.li.mahidol.ac.th/handle/123456789/31411 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84886408136&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Biochemistry, Genetics and Molecular Biology
Chemistry
spellingShingle Biochemistry, Genetics and Molecular Biology
Chemistry
Sirirat Kumarn
Nitirat Chimnoi
Somsak Ruchirawat
Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
description A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisation. It provides access to useful quantities of 1 in 16 steps and 19% overall yield, based on the manufacturer's stated resin substitution from commercially available materials, and also verifies the absolute stereochemistry of the natural product. © The Royal Society of Chemistry 2013.
author2 Mahidol University
author_facet Mahidol University
Sirirat Kumarn
Nitirat Chimnoi
Somsak Ruchirawat
format Article
author Sirirat Kumarn
Nitirat Chimnoi
Somsak Ruchirawat
author_sort Sirirat Kumarn
title Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
title_short Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
title_full Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
title_fullStr Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
title_full_unstemmed Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach
title_sort synthesis of integerrimide a by an on-resin tandem fmoc-deprotection- macrocyclisation approach
publishDate 2018
url https://repository.li.mahidol.ac.th/handle/123456789/31411
_version_ 1763490239390679040

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