Abstract

Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.

Original languageEnglish
Pages (from-to)2544-2551
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume7
Issue number12
DOIs
Publication statusPublished - 1 Dec 2018

Fingerprint

Natural polymers
Acetylglucosamine
Disaccharides
Chitin
Peptidoglycan
Scaffolds
Polymers
Carbohydrates
Atoms
chitobiose

Keywords

  • acetylglucosamine
  • chitin
  • chitooligosaccharides
  • NAG-NAM
  • regioselective protection

Cite this

@article{ef4375ba00ff4cb097fb25ebe27f4402,
title = "From a Natural Polymer to Relevant NAG-NAM Precursors",
abstract = "Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.",
keywords = "acetylglucosamine, chitin, chitooligosaccharides, NAG-NAM, regioselective protection",
author = "Carvalho, {Lu{\'i}sa C. R.} and Fausto Queda and Almeida, {C{\'a}tia V.} and Filipe, {S{\'e}rgio R.} and Marques, {M. Manuel B.}",
note = "info:eu-repo/grantAgreement/FCT/5876/147218/PT# This work was funded by Fundacao para a Ciencia e Tecnologia (FC&T) for: fellowship PD/BD/109632/2015. The Associate Laboratory Research Unit for Green Chemistry - Technologies and Processes Clean - LAQV financed by national funds from FCT/MEC (UID/QUI/50006/2013) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER - 007265). The National NMR Facility, supported by FC&T (RECI/BBB- BQB/0230/2012). iNOVA4 Health Research Unit (LISBOA-01-0145-FEDER-007344), is co-funded by FC&T/Ministerio da Ciencia e do Ensino Superior, and by FEDER under the PT2020 Partnership Agreement.",
year = "2018",
month = "12",
day = "1",
doi = "10.1002/ajoc.201800592",
language = "English",
volume = "7",
pages = "2544--2551",
journal = "Asian Journal of Organic Chemistry",
issn = "2193-5807",
publisher = "Wiley-VCH Verlag",
number = "12",

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T1 - From a Natural Polymer to Relevant NAG-NAM Precursors

AU - Carvalho, Luísa C. R.

AU - Queda, Fausto

AU - Almeida, Cátia V.

AU - Filipe, Sérgio R.

AU - Marques, M. Manuel B.

N1 - info:eu-repo/grantAgreement/FCT/5876/147218/PT# This work was funded by Fundacao para a Ciencia e Tecnologia (FC&T) for: fellowship PD/BD/109632/2015. The Associate Laboratory Research Unit for Green Chemistry - Technologies and Processes Clean - LAQV financed by national funds from FCT/MEC (UID/QUI/50006/2013) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER - 007265). The National NMR Facility, supported by FC&T (RECI/BBB- BQB/0230/2012). iNOVA4 Health Research Unit (LISBOA-01-0145-FEDER-007344), is co-funded by FC&T/Ministerio da Ciencia e do Ensino Superior, and by FEDER under the PT2020 Partnership Agreement.

PY - 2018/12/1

Y1 - 2018/12/1

N2 - Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.

AB - Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.

KW - acetylglucosamine

KW - chitin

KW - chitooligosaccharides

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KW - regioselective protection

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