Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides

[Image: see text] A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopol...

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Autores principales: Wang, Liming, Zhang, Yongzhen, Overkleeft, Herman S., van der Marel, Gijsbert A., Codée, Jeroen D. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7754192/
https://www.ncbi.nlm.nih.gov/pubmed/32375481
http://dx.doi.org/10.1021/acs.joc.0c00703
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author Wang, Liming
Zhang, Yongzhen
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
author_facet Wang, Liming
Zhang, Yongzhen
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
author_sort Wang, Liming
collection PubMed
description [Image: see text] A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-α-(1,4)-glucosazide] disaccharide building blocks were synthesized using a 4,6-O-DTBS protected galactosyl azide donor.
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spelling pubmed-77541922020-12-23 Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides Wang, Liming Zhang, Yongzhen Overkleeft, Herman S. van der Marel, Gijsbert A. Codée, Jeroen D. C. J Org Chem [Image: see text] A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-α-(1,4)-glucosazide] disaccharide building blocks were synthesized using a 4,6-O-DTBS protected galactosyl azide donor. American Chemical Society 2020-05-07 2020-12-18 /pmc/articles/PMC7754192/ /pubmed/32375481 http://dx.doi.org/10.1021/acs.joc.0c00703 Text en This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Wang, Liming
Zhang, Yongzhen
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title_full Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title_fullStr Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title_full_unstemmed Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title_short Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
title_sort reagent controlled glycosylations for the assembly of well-defined pel oligosaccharides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7754192/
https://www.ncbi.nlm.nih.gov/pubmed/32375481
http://dx.doi.org/10.1021/acs.joc.0c00703
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