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Semi-synthesis of a 3-O-sulfated red seaweed galactan-derived disaccharide alditol.
Carbohydr Res. 2006 Jul 24; 341(10):1753-7.CR

Abstract

Beta-D-Galp3-SO3-(1-->4)-3,6-anhydro-L-GalOH (agarobiitol 3(2)-sulfate, 4) was semi-synthetically prepared as follows: production of agarobiitol (1) from agarose by partial reductive hydrolysis, protection of the primary hydroxyl groups of 1 with trityl groups to produce the 1(1),6(2)-di-O-tritylated derivative (2), regioselective dibutylstannylene-mediated sulfation of 2 to give the 3(2)-O-sulfated-1(1),6(2)-di-O-tritylated compound (3), and detritylation of compound 3 to give the final product (4). This semi-synthetic route allowed the preparation of a red seaweed galactan-derived disaccharide alditol with sulfate group located at C-3 of the galactopyranosidic ring. Because red seaweed galactans are glycosidically linked at C-3 of the beta-D-Galp unit, a sulfated derivative with this structure could not be obtained by partial reductive hydrolysis of sulfated red seaweed galactans.

Authors+Show Affiliations

Gonçalves AG
Department of Chemistry, Dalhousie University, Halifax, NS, Canada B3H 4J3.
Noseda MD
No affiliation info available
Duarte ME
No affiliation info available
Grindley TB
No affiliation info available

MeSH

Carbohydrate SequenceDisaccharidesGalactansMolecular Sequence DataRhodophyta

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16516874

Citation

Gonçalves, Alan G., et al. "Semi-synthesis of a 3-O-sulfated Red Seaweed Galactan-derived Disaccharide Alditol." Carbohydrate Research, vol. 341, no. 10, 2006, pp. 1753-7.
Gonçalves AG, Noseda MD, Duarte ME, et al. Semi-synthesis of a 3-O-sulfated red seaweed galactan-derived disaccharide alditol. Carbohydr Res. 2006;341(10):1753-7.
Gonçalves, A. G., Noseda, M. D., Duarte, M. E., & Grindley, T. B. (2006). Semi-synthesis of a 3-O-sulfated red seaweed galactan-derived disaccharide alditol. Carbohydrate Research, 341(10), 1753-7.
Gonçalves AG, et al. Semi-synthesis of a 3-O-sulfated Red Seaweed Galactan-derived Disaccharide Alditol. Carbohydr Res. 2006 Jul 24;341(10):1753-7. PubMed PMID: 16516874.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Semi-synthesis of a 3-O-sulfated red seaweed galactan-derived disaccharide alditol. AU - Gonçalves,Alan G, AU - Noseda,Miguel D, AU - Duarte,M Eugênia R, AU - Grindley,T Bruce, Y1 - 2006/03/03/ PY - 2005/12/28/received PY - 2006/02/01/revised PY - 2006/02/06/accepted PY - 2006/3/7/pubmed PY - 2006/8/29/medline PY - 2006/3/7/entrez SP - 1753 EP - 7 JF - Carbohydrate research JO - Carbohydr Res VL - 341 IS - 10 N2 - Beta-D-Galp3-SO3-(1-->4)-3,6-anhydro-L-GalOH (agarobiitol 3(2)-sulfate, 4) was semi-synthetically prepared as follows: production of agarobiitol (1) from agarose by partial reductive hydrolysis, protection of the primary hydroxyl groups of 1 with trityl groups to produce the 1(1),6(2)-di-O-tritylated derivative (2), regioselective dibutylstannylene-mediated sulfation of 2 to give the 3(2)-O-sulfated-1(1),6(2)-di-O-tritylated compound (3), and detritylation of compound 3 to give the final product (4). This semi-synthetic route allowed the preparation of a red seaweed galactan-derived disaccharide alditol with sulfate group located at C-3 of the galactopyranosidic ring. Because red seaweed galactans are glycosidically linked at C-3 of the beta-D-Galp unit, a sulfated derivative with this structure could not be obtained by partial reductive hydrolysis of sulfated red seaweed galactans. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/16516874/Semi_synthesis_of_a_3_O_sulfated_red_seaweed_galactan_derived_disaccharide_alditol_ DB - PRIME DP - Unbound Medicine ER -