Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors
An assessment of the relative O-3/O-4 reactivities of both methyl α- and β-d-glycosides of N-dimethylmaleoyl (DMM) d-glucosamine acceptors protected at O-6 with benzoyl (Bz), benzyl (Bn), and tert-butyldiphenylsilyl (TBDPS) groups is presented using per-O-benzoylated β-d-galactofuranosyl and per-O-a...
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| Publicado: |
2007
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v342_n17_p2522_Bohn http://hdl.handle.net/20.500.12110/paper_00086215_v342_n17_p2522_Bohn |
| Aporte de: |
| id |
paper:paper_00086215_v342_n17_p2522_Bohn |
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| record_format |
dspace |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Galactofuranosyl donor Galactopyranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Regioselectivity Galactofuranosyl donors Galactopyranosyl donors Glucosamine acceptors N-Dimethylmaleoyl group Amines Reaction kinetics Regioselectivity Glycosylation alpha methylglucoside beta methylglucoside glucosamine methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 benzoyl 2deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butydiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzolyl beta dextro galactofuranosy (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethlmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosy (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleidomido beta dextro glycopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimenthylmaleido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 dimethylmaleimido beta dextro glucopyranoside Methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o tert butyldiphenysilly 2 deoxy 2 dimenthylmaleido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmealeimido betal dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta galactofuranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido dextro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha detxro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside unclassified drug amino acid substitution article carbohydrate analysis diastereoisomer enantioselectivity glycosylation priority journal protein domain Carbohydrate Conformation Carbohydrate Sequence Disaccharides Electrochemistry Glucosamine Glycosides Glycosylation Glycosyltransferases Isomerism Magnetic Resonance Spectroscopy Models, Chemical Molecular Conformation Molecular Sequence Data Molecular Structure Polysaccharides |
| spellingShingle |
Galactofuranosyl donor Galactopyranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Regioselectivity Galactofuranosyl donors Galactopyranosyl donors Glucosamine acceptors N-Dimethylmaleoyl group Amines Reaction kinetics Regioselectivity Glycosylation alpha methylglucoside beta methylglucoside glucosamine methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 benzoyl 2deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butydiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzolyl beta dextro galactofuranosy (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethlmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosy (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleidomido beta dextro glycopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimenthylmaleido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 dimethylmaleimido beta dextro glucopyranoside Methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o tert butyldiphenysilly 2 deoxy 2 dimenthylmaleido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmealeimido betal dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta galactofuranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido dextro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha detxro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside unclassified drug amino acid substitution article carbohydrate analysis diastereoisomer enantioselectivity glycosylation priority journal protein domain Carbohydrate Conformation Carbohydrate Sequence Disaccharides Electrochemistry Glucosamine Glycosides Glycosylation Glycosyltransferases Isomerism Magnetic Resonance Spectroscopy Models, Chemical Molecular Conformation Molecular Sequence Data Molecular Structure Polysaccharides Stortz, Carlos Arturo Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| topic_facet |
Galactofuranosyl donor Galactopyranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Regioselectivity Galactofuranosyl donors Galactopyranosyl donors Glucosamine acceptors N-Dimethylmaleoyl group Amines Reaction kinetics Regioselectivity Glycosylation alpha methylglucoside beta methylglucoside glucosamine methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 benzoyl 2deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butydiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzolyl beta dextro galactofuranosy (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethlmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosy (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleidomido beta dextro glycopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimenthylmaleido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 dimethylmaleimido beta dextro glucopyranoside Methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o tert butyldiphenysilly 2 deoxy 2 dimenthylmaleido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmealeimido betal dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta galactofuranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido dextro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha detxro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside unclassified drug amino acid substitution article carbohydrate analysis diastereoisomer enantioselectivity glycosylation priority journal protein domain Carbohydrate Conformation Carbohydrate Sequence Disaccharides Electrochemistry Glucosamine Glycosides Glycosylation Glycosyltransferases Isomerism Magnetic Resonance Spectroscopy Models, Chemical Molecular Conformation Molecular Sequence Data Molecular Structure Polysaccharides |
| description |
An assessment of the relative O-3/O-4 reactivities of both methyl α- and β-d-glycosides of N-dimethylmaleoyl (DMM) d-glucosamine acceptors protected at O-6 with benzoyl (Bz), benzyl (Bn), and tert-butyldiphenylsilyl (TBDPS) groups is presented using per-O-benzoylated β-d-galactofuranosyl and per-O-acetylated α-d-galactopyranosyl trichloroacetimidates as glycosyl donors. Using the former donor, the α anomer of the 6-O-benzoylated compound gave exclusive substitution at O-3, whereas the other two compounds with α-configuration kept this site as preferential. The β anomer of the 6-O-benzoylated compound gave the same amounts of reaction products on O-3 and O-4, whereas the other β analogs carried a more reactive O-4. The same reactions were carried out using as donor the less-reactive per-O-acetylated α-d-galactopyranosyl trichloroacetimidate. Although the same trend was found to occur, the O-4 was always relatively more reactive with the pyranosyl donor than with the furanosyl donor, when keeping the remaining factors constant. Furthermore, the β anomers of the acceptor gave almost exclusive substitution at O-4. These observations confirm and extend the utility of these 'matching' donor and acceptor reactivities. © 2007 Elsevier Ltd. All rights reserved. |
| author |
Stortz, Carlos Arturo |
| author_facet |
Stortz, Carlos Arturo |
| author_sort |
Stortz, Carlos Arturo |
| title |
Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| title_short |
Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| title_full |
Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| title_fullStr |
Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| title_full_unstemmed |
Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors |
| title_sort |
differential o-3/o-4 regioselectivity in the glycosylation of α and β anomers of 6-o-substituted n-dimethylmaleoyl-protected d-glucosamine acceptors |
| publishDate |
2007 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v342_n17_p2522_Bohn http://hdl.handle.net/20.500.12110/paper_00086215_v342_n17_p2522_Bohn |
| work_keys_str_mv |
AT stortzcarlosarturo differentialo3o4regioselectivityintheglycosylationofaandbanomersof6osubstitutedndimethylmaleoylprotecteddglucosamineacceptors |
| _version_ |
1768541588290535424 |
| spelling |
paper:paper_00086215_v342_n17_p2522_Bohn2023-06-08T14:32:53Z Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors Stortz, Carlos Arturo Galactofuranosyl donor Galactopyranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Regioselectivity Galactofuranosyl donors Galactopyranosyl donors Glucosamine acceptors N-Dimethylmaleoyl group Amines Reaction kinetics Regioselectivity Glycosylation alpha methylglucoside beta methylglucoside glucosamine methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-3) 4 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 benzoyl 2deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleidmido alpha dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butydiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,4,6 tetra o acetyl beta dextro galactopyranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzolyl beta dextro galactofuranosy (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethlmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosy (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleidomido beta dextro glycopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimenthylmaleido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o benzyl 2 dimethylmaleimido beta dextro glucopyranoside Methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-3) 4 o acetyl 6 o tert butyldiphenysilly 2 deoxy 2 dimenthylmaleido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl (1-4) 3 o acetyl 6 o benzyl 2 deoxy 2 dimethylmealeimido betal dextro glucopyranoside methyl 2,3,5,6 tetra o benzoyl beta galactofuranosyl (1-4) 3 o acetyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido alpha dextro glucopyranoside methyl 6 o benzoyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha glucopyranoside methyl 6 o benzyl 2 deoxy 2 dimethylmaleimido dextro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido alpha detxro glucopyranoside methyl 6 o tert butyldiphenylsilyl 2 deoxy 2 dimethylmaleimido beta dextro glucopyranoside unclassified drug amino acid substitution article carbohydrate analysis diastereoisomer enantioselectivity glycosylation priority journal protein domain Carbohydrate Conformation Carbohydrate Sequence Disaccharides Electrochemistry Glucosamine Glycosides Glycosylation Glycosyltransferases Isomerism Magnetic Resonance Spectroscopy Models, Chemical Molecular Conformation Molecular Sequence Data Molecular Structure Polysaccharides An assessment of the relative O-3/O-4 reactivities of both methyl α- and β-d-glycosides of N-dimethylmaleoyl (DMM) d-glucosamine acceptors protected at O-6 with benzoyl (Bz), benzyl (Bn), and tert-butyldiphenylsilyl (TBDPS) groups is presented using per-O-benzoylated β-d-galactofuranosyl and per-O-acetylated α-d-galactopyranosyl trichloroacetimidates as glycosyl donors. Using the former donor, the α anomer of the 6-O-benzoylated compound gave exclusive substitution at O-3, whereas the other two compounds with α-configuration kept this site as preferential. The β anomer of the 6-O-benzoylated compound gave the same amounts of reaction products on O-3 and O-4, whereas the other β analogs carried a more reactive O-4. The same reactions were carried out using as donor the less-reactive per-O-acetylated α-d-galactopyranosyl trichloroacetimidate. Although the same trend was found to occur, the O-4 was always relatively more reactive with the pyranosyl donor than with the furanosyl donor, when keeping the remaining factors constant. Furthermore, the β anomers of the acceptor gave almost exclusive substitution at O-4. These observations confirm and extend the utility of these 'matching' donor and acceptor reactivities. © 2007 Elsevier Ltd. All rights reserved. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2007 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v342_n17_p2522_Bohn http://hdl.handle.net/20.500.12110/paper_00086215_v342_n17_p2522_Bohn |