Abstract
An unprecedented approach towards oligosaccharides containing N-acetylglucosamine-N-acetylmuramic (NAG-NAM) units was developed. These novel bacterial cell wall surrogates were obtained from chitosan via a top down approach involving both chemical and enzymatic reactions. The chemical modification of chitosan using a molecular clamp based strategy, allowed obtaining N-acetylglucosamine-N-acetylmuramic (NAG-NAM) containing oligomers. Intercalation of NAM residues was confirmed through the analysis of oligosaccharide fragments from enzymatic digestion and it was found that this route affords NAG-NAM containing oligosaccharides in 33% yield. These oligosaccharides mimic the carbohydrate basic skeleton of most bacterial cell surfaces. The oligosaccharides prepared are biologically relevant and will serve as a platform for further molecular recognition studies with different receptors and enzymes of both bacterial cell wall and innate immune system. This strategy combining both chemical modification and enzymatic digestion provides a novel and simple route for an easy access to bacterial cell wall fragments – biologically important targets.
| Original language | English |
|---|---|
| Article number | 115133 |
| Journal | Carbohydrate Polymers |
| Volume | 224 |
| DOIs | |
| Publication status | Published - 15 Nov 2019 |
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Keywords
- Chemo-enzymatic
- Chitooligosaccharides
- Chitosan
- Regioselective modification
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A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template. / Queda, Fausto; Covas, Gonçalo; Silva, Tomé; Santos, Cátia Almeida; Bronze, Maria R.; Cañada, Francisco Javier; Corvo, Marta C.; Filipe, Sérgio R.; Marques, M. Manuel B.
In: Carbohydrate Polymers, Vol. 224, 115133, 15.11.2019.Research output: Contribution to journal › Article
TY - JOUR
T1 - A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template
AU - Queda, Fausto
AU - Covas, Gonçalo
AU - Silva, Tomé
AU - Santos, Cátia Almeida
AU - Bronze, Maria R.
AU - Cañada, Francisco Javier
AU - Corvo, Marta C.
AU - Filipe, Sérgio R.
AU - Marques, M. Manuel B.
N1 - info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F89518%2F2012/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127730/PT# info:eu-repo/grantAgreement/FCT/5876/147348/PT# SFRH/BD/52207/2013 (to FQ and GC) Associate Laboratory for Green Chemistry- LAQV which is financed by national funds from FCT/MCTES (UID/QUI/50006/2019) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER - 007265). i3N|Cenitmat is financed by national funds from FC&T/MEC (UID/CTM/50025/2019) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007688). The National NMR Facility is supported by FC&T (ROTEIRO/0031/2013 – PINFRA/22161/2016, co-financed by FEDER through COMPETE 2020, POCI, and PORL and FC&T through PIDDAC). iNOVA4 Health Research Unit (LISBOA-01-0145-FEDER-007344), is co-funded by FC&T/Ministério da Ciência e do Ensino Superior , and by FEDER under the PT2020 Partnership Agreement. CTQ2012‐32025 and CTQ2015-64597-C2 of Spanish Ministry of Economy and Competitiveness to FJC are acknowledge. The LC–MS/MS equipment is part of The National MS Facility, supported by FC&T (REDE/1518/REM/2005). This work was supported by the Applied Molecular Biosciences Unit-UCIBIO which is financed by national funds from FCT/MCTES (UID/Multi/04378/2019).
PY - 2019/11/15
Y1 - 2019/11/15
N2 - An unprecedented approach towards oligosaccharides containing N-acetylglucosamine-N-acetylmuramic (NAG-NAM) units was developed. These novel bacterial cell wall surrogates were obtained from chitosan via a top down approach involving both chemical and enzymatic reactions. The chemical modification of chitosan using a molecular clamp based strategy, allowed obtaining N-acetylglucosamine-N-acetylmuramic (NAG-NAM) containing oligomers. Intercalation of NAM residues was confirmed through the analysis of oligosaccharide fragments from enzymatic digestion and it was found that this route affords NAG-NAM containing oligosaccharides in 33% yield. These oligosaccharides mimic the carbohydrate basic skeleton of most bacterial cell surfaces. The oligosaccharides prepared are biologically relevant and will serve as a platform for further molecular recognition studies with different receptors and enzymes of both bacterial cell wall and innate immune system. This strategy combining both chemical modification and enzymatic digestion provides a novel and simple route for an easy access to bacterial cell wall fragments – biologically important targets.
AB - An unprecedented approach towards oligosaccharides containing N-acetylglucosamine-N-acetylmuramic (NAG-NAM) units was developed. These novel bacterial cell wall surrogates were obtained from chitosan via a top down approach involving both chemical and enzymatic reactions. The chemical modification of chitosan using a molecular clamp based strategy, allowed obtaining N-acetylglucosamine-N-acetylmuramic (NAG-NAM) containing oligomers. Intercalation of NAM residues was confirmed through the analysis of oligosaccharide fragments from enzymatic digestion and it was found that this route affords NAG-NAM containing oligosaccharides in 33% yield. These oligosaccharides mimic the carbohydrate basic skeleton of most bacterial cell surfaces. The oligosaccharides prepared are biologically relevant and will serve as a platform for further molecular recognition studies with different receptors and enzymes of both bacterial cell wall and innate immune system. This strategy combining both chemical modification and enzymatic digestion provides a novel and simple route for an easy access to bacterial cell wall fragments – biologically important targets.
KW - Chemo-enzymatic
KW - Chitooligosaccharides
KW - Chitosan
KW - Regioselective modification
UR - http://www.scopus.com/inward/record.url?scp=85070111050&partnerID=8YFLogxK
U2 - 10.1016/j.carbpol.2019.115133
DO - 10.1016/j.carbpol.2019.115133
M3 - Article
VL - 224
JO - Carbohydrate Polymers
JF - Carbohydrate Polymers
SN - 0144-8617
M1 - 115133
ER -