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Abstract:

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.

Registro:

Documento: Artículo
Título:Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors
Autor:Bohn, M.L.; Colombo, M.I.; Pisano, P.L.; Stortz, C.A.; Rúveda, E.A.
Filiación:Instituto de Química Orgánica y de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina
Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pab. 2, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2007
Volumen:342
Número:17
Página de inicio:2522
Página de fin:2536
DOI: http://dx.doi.org/10.1016/j.carres.2007.08.006
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:alpha methylglucoside, 97-30-3; glucosamine, 3416-24-8, 4607-22-1; Disaccharides; Glucosamine, 3416-24-8; Glycosides; Glycosyltransferases, 2.4.-; Polysaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v342_n17_p2522_Bohn

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Citas:

---------- APA ----------
Bohn, M.L., Colombo, M.I., Pisano, P.L., Stortz, C.A. & Rúveda, E.A. (2007) . Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors. Carbohydrate Research, 342(17), 2522-2536.
http://dx.doi.org/10.1016/j.carres.2007.08.006
---------- CHICAGO ----------
Bohn, M.L., Colombo, M.I., Pisano, P.L., Stortz, C.A., Rúveda, E.A. "Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors" . Carbohydrate Research 342, no. 17 (2007) : 2522-2536.
http://dx.doi.org/10.1016/j.carres.2007.08.006
---------- MLA ----------
Bohn, M.L., Colombo, M.I., Pisano, P.L., Stortz, C.A., Rúveda, E.A. "Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors" . Carbohydrate Research, vol. 342, no. 17, 2007, pp. 2522-2536.
http://dx.doi.org/10.1016/j.carres.2007.08.006
---------- VANCOUVER ----------
Bohn, M.L., Colombo, M.I., Pisano, P.L., Stortz, C.A., Rúveda, E.A. Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors. Carbohydr. Res. 2007;342(17):2522-2536.
http://dx.doi.org/10.1016/j.carres.2007.08.006