From a Natural Polymer to Relevant NAG‐NAM Precursors

Carvalho, Luísa C. R.; Queda, Fausto; Almeida, Cátia V.; Filipe, Sérgio R.; Marques, M. Manuel B.

doi:10.1002/ajoc.201800592

Cited by 6 publications

(14 citation statements)

References 47 publications

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Section: Synthetic Approaches Towards the Carbohydrate Backbone Ofmentioning

confidence: 99%

“… Synthesis of the NAG-NAM precursor 66 from peracetylated chitobiose 63 reported by Marques group [ 79 ]. ( a ) Ac 2 O, H 2 SO 4 , 55 °C, 3 h, then r.t., 16 h, and 55 °C, 1 h, 13%; ( b ) TFAA, Pyr, 120 °C, 15 min, 76%; ( c ) TolSH, BF 3 OEt 2 , DCM, r.t., overnight, 80%; ( d ) (1) MeONa, MeOH, r.t., overnight.…”

Section: Figures and Schemesmentioning

confidence: 99%

“…In 2018 we established a procedure to achieve an advanced precursor of the NAG-NAM unit via orthogonal synthesis, from peracetylated chitobiose, obtained after chitin chemical hydrolysis, as shown in Scheme 11 [79]. During recent years, our group embraced the challenge of synthetizing NAG-NAM containing oligosaccharides and its precursors, using as starting material biopolymers, with the β-1,4 glycosidic bond already installed.…”

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

confidence: 99%

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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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Section: Synthetic Approaches Towards the Carbohydrate Backbone Ofmentioning

confidence: 99%

Section: Figures and Schemesmentioning

confidence: 99%

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

confidence: 99%

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Assembly of Peptidoglycan Fragments—A Synthetic Challenge

et al. 2020

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“…Deacetylated chitin or chitosan could therefore be a potential precursor if one attempts to semisynthetically mimic the structure of peptidoglycans. 3 Such mimetics can be of interest for studying phenomena at interfaces such as adsorption, 4 enzymatic digestion, 5 live-cell adhesion, 6 or lithography. 7 , 8 A defined semisynthetic peptidoglycan coating could also contribute to insights into biological pattern recognition, 9 cell–cell communication, 10 , 11 or immune response 12 and can increase our understanding of bacteria.…”

Section: Introductionmentioning

confidence: 99%

Solid Phase Peptide Synthesis on Chitosan Thin Films

et al. 2022

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Stable chitosan thin films can be promising substrates for creating nanometric peptide-bound polyglucosamine layers. Those are of scientific interest since they can have certain structural similarities to bacterial peptidoglycans. Such films were deposited by spin coating from chitosan solutions and modified by acetylation and N -protected amino acids. The masses of deposited materials and their stability in aqueous solutions at different pH values and water interaction were determined with a quartz crystal microbalance with dissipation (QCM-D). The evolution of the surface composition was followed by X-ray photoelectron (XPS) and attenuated total reflectance infrared (ATR-IR) spectroscopy. Morphological changes were measured by atomic force microscopy (AFM), while the surface wettability was monitored by by static water contact angle measurements. The combination of the characterization techniques enabled an insight into the surface chemistry for each treatment step and confirmed the acetylation and coupling of N -protected glycine peptides. The developed procedures are seen as first steps toward preparing thin layers of acetylated chitin, potentially imitating the nanometric peptide substituted glycan layers found in bacterial cell walls.

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“…This methodology has recently been summarized by Marques et al who proposed a rapid access to NAG-NAM precursor starting from chitinbiose disaccharide and avoiding the tricky step of monosaccharide coupling. [8] Starting from di-N-TFA-S-tolylchitobioside, this original strategy necessitates in the first and key step the discrimination of O-3 I position with the help of 1,2-diacetal methodology allowing the selective protection of O-3 II and O-4 II positions. [9] Then protection of O-6 I and O-6 II positions can be achieved with bulky silyl protecting group such as tert-butyldimethylsilyl (TBDMS).…”

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confidence: 99%

A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis

et al. 2021

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Peptidoglycan oligomers constitute precious tools for the biochemical and structural studies of enzymes involved in the bacterial cell wall metabolism. In this study we show that an unprecedented selective Zemplén de-O-acetylation of benzyl chitinbioside peracetate leads to a fast and efficient route to N-acetylmuramyl (1→4) Nacetylglucosaminide disaccharide, a central building block for the synthesis of peptidoglycan oligomers. Starting from known benzyl chitinbioside, NAG-NAM disaccharide pentapeptide is prepared in seven steps with an overall yield of 12%.

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From a Natural Polymer to Relevant NAG‐NAM Precursors

Cited by 6 publications

References 47 publications

Assembly of Peptidoglycan Fragments—A Synthetic Challenge

Assembly of Peptidoglycan Fragments—A Synthetic Challenge

Solid Phase Peptide Synthesis on Chitosan Thin Films

A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis

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