TY - JOUR
T1 - From a Natural Polymer to Relevant NAG-NAM Precursors
AU - Carvalho, Luísa C. R.
AU - Queda, Fausto
AU - Filipe, Sérgio R.
AU - Marques, M. Manuel B.
AU - Santos, Cátia V. Almeida
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
KW - NAG-NAM
KW - regioselective protection
UR - http://www.scopus.com/inward/record.url?scp=85056810823&partnerID=8YFLogxK
U2 - 10.1002/ajoc.201800592
DO - 10.1002/ajoc.201800592
M3 - Article
AN - SCOPUS:85056810823
SN - 2193-5807
VL - 7
SP - 2544
EP - 2551
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 12
ER -