A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template

Queda, Fausto; Covas, Gonçalo; Silva, Tomé S.; Santos, Conceição; Bronze, Maria Rosário; Cañada, F. Javier; Corvo, Marta C.; Filipe, Sérgio R.; Marques, M. Manuel B.

doi:10.1016/j.carbpol.2019.115133

Cited by 9 publications

(6 citation statements)

References 60 publications

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“…O resultado da hidrólise enzimática foi avaliado por HPLC e LC-MS. Após esta análise foi possível concluir que 33% do polímero modificado havia sido digerido por estas enzimas, tendo sido identificados, como produtos maioritários, o dissacárido NAG-NAM, bem como o trissacárido NAG-NAG-NAM. Ao mesmo tempo, o polímero modificado mostrou ser capaz de co-precipitar com proteínas PGRPs (do inglês Peptidoglycan Recognition Proteins), que são capazes de reconhecer peptidoglicano [6].…”

Section: Maria Manuel Marquesunclassified

Quitina e Quitosano: Substratos para Síntese Química de Peptidoglicano

Queda¹,

Filipe²,

Marques³

2023

BSPQuimica

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Section: Maria Manuel Marquesunclassified

Quitina e Quitosano: Substratos para Síntese Química de Peptidoglicano

Queda¹,

Filipe²,

Marques³

2023

BSPQuimica

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“…In the follow-up of our synthesis of an advanced NAG-NAM precursor from chitobiose, we next reported the synthesis of NAG-NAM-containing oligosaccharides from chitosan via a top-down approach involving both chemical and enzymatic reactions (Scheme 12) [83]. This new route was able In our strategy, we took advantage of the already established β-1,4 glycosidic bond present in the easily-obtained peracetylated chitobiose 63, avoiding one of the most challenging steps in the synthesis of PGN fragments.…”

Section: Synthetic Approaches Towards the Carbohydrate Backbone Of Pgn From Biopolymersmentioning

confidence: 99%

“…In the follow-up of our synthesis of an advanced NAG-NAM precursor from chitobiose, we next reported the synthesis of NAG-NAM-containing oligosaccharides from chitosan via a top-down approach involving both chemical and enzymatic reactions (Scheme 12) [83]. This new route was able to overcome the difficulties in obtaining sufficient long fragments to replace samples of biological origin, which also constituted a limitation for further biological investigations [9].…”

Section: Synthetic Approaches Towards the Carbohydrate Backbone Of Pgn From Biopolymersmentioning

confidence: 99%

Assembly of Peptidoglycan Fragments—A Synthetic Challenge

et al. 2020

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Peptidoglycan (PGN) is a major constituent of most bacterial cell walls that is recognized as a primary target of the innate immune system. The availability of pure PGN molecules has become key to different biological studies. This review aims to (1) provide an overview of PGN biosynthesis, focusing on the main biosynthetic intermediates; (2) focus on the challenges for chemical synthesis posed by the unique and complex structure of PGN; and (3) cover the synthetic routes of PGN fragments developed to date. The key difficulties in the synthesis of PGN molecules mainly involve stereoselective glycosylation involving NAG derivatives. The complex synthesis of the carbohydrate backbone commonly involves multistep sequences of chemical reactions to install the lactyl moiety at the O-3 position of NAG derivatives and to control enantioselective glycosylation. Recent advances are presented and synthetic routes are described according to the main strategy used: (i) based on the availability of starting materials such as glucosamine derivatives; (ii) based on a particular orthogonal synthesis; and (iii) based on the use of other natural biopolymers as raw materials.

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“…First, the amino groups of CMCs can bind to the bacterial cell wall, leading to its destruction. 50 Additionally, PA is generally recognized by its antimicrobial effects. 51 Last, Ga 3+ is a broad-spectrum antibacterial agent.…”

Section: ■ Introductionmentioning

confidence: 99%

Multifunctional Porous Bilayer Artificial Skin for Enhanced Wound Healing

Xia,

Yan,

Wei

et al. 2024

ACS Appl. Mater. Interfaces

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A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template

Cited by 9 publications

References 60 publications

Quitina e Quitosano: Substratos para Síntese Química de Peptidoglicano

Quitina e Quitosano: Substratos para Síntese Química de Peptidoglicano

Assembly of Peptidoglycan Fragments—A Synthetic Challenge

Multifunctional Porous Bilayer Artificial Skin for Enhanced Wound Healing

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