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Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes.
Org Biomol Chem. 2009 Feb 07; 7(3):576-88.OB

Abstract

Agarans and carrageenans are abundant natural polysaccharides which are obtained on a large scale by water extraction from a variety of red seaweeds. These galactans, in addition to being valuable products for the pharmaceutical and food industries, are low cost starting materials for the preparation of useful and rare carbohydrate-based building blocks whose access by total synthesis is difficult and expensive. The semisynthesis of two sets of C-glycosyl aldehydes with l- and d-configuration from agarose and kappa-carrageenan respectively is described. Succinctly, the partial acid-catalyzed mercaptolysis of the two galactans under mild conditions afforded agarobiose and carrabiose (beta-d-Galp-(1-->4)-3,6-anhydro-aldehydo-l- and d-galactose, respectively) derivatives. Complete depolymerization of agarose and kappa-carrageenan under harsher conditions produced 3,6-anhydro l- and d-galactose aldehyde derivatives. Chain shortening of these products via alditol formation and oxidative carbon-carbon bond cleavage furnished C-formyl alpha-l- and alpha-d-threofuranosides. The above C-glycosyl aldehydes were all prepared on a meaningful preparative scale starting from gram quantities of galactans. Finally, a new procedure for the preparation of the 2,3-O-benzyl l-threofuranose was established by Baeyer-Villiger oxidation of the benzylated C-formyl alpha-l-threofuranoside here prepared from agarose.

Authors+Show Affiliations

Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

19156325

Citation

Ducatti, Diogo R B., et al. "Production of Carbohydrate Building Blocks From Red Seaweed Polysaccharides. Efficient Conversion of Galactans Into C-glycosyl Aldehydes." Organic & Biomolecular Chemistry, vol. 7, no. 3, 2009, pp. 576-88.
Ducatti DR, Massi A, Noseda MD, et al. Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes. Org Biomol Chem. 2009;7(3):576-88.
Ducatti, D. R., Massi, A., Noseda, M. D., Duarte, M. E., & Dondoni, A. (2009). Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes. Organic & Biomolecular Chemistry, 7(3), 576-88. https://doi.org/10.1039/b816606d
Ducatti DR, et al. Production of Carbohydrate Building Blocks From Red Seaweed Polysaccharides. Efficient Conversion of Galactans Into C-glycosyl Aldehydes. Org Biomol Chem. 2009 Feb 7;7(3):576-88. PubMed PMID: 19156325.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes. AU - Ducatti,Diogo R B, AU - Massi,Alessandro, AU - Noseda,Miguel D, AU - Duarte,Maria Eugênia R, AU - Dondoni,Alessandro, Y1 - 2008/11/26/ PY - 2009/1/22/entrez PY - 2009/1/22/pubmed PY - 2009/3/11/medline SP - 576 EP - 88 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 7 IS - 3 N2 - Agarans and carrageenans are abundant natural polysaccharides which are obtained on a large scale by water extraction from a variety of red seaweeds. These galactans, in addition to being valuable products for the pharmaceutical and food industries, are low cost starting materials for the preparation of useful and rare carbohydrate-based building blocks whose access by total synthesis is difficult and expensive. The semisynthesis of two sets of C-glycosyl aldehydes with l- and d-configuration from agarose and kappa-carrageenan respectively is described. Succinctly, the partial acid-catalyzed mercaptolysis of the two galactans under mild conditions afforded agarobiose and carrabiose (beta-d-Galp-(1-->4)-3,6-anhydro-aldehydo-l- and d-galactose, respectively) derivatives. Complete depolymerization of agarose and kappa-carrageenan under harsher conditions produced 3,6-anhydro l- and d-galactose aldehyde derivatives. Chain shortening of these products via alditol formation and oxidative carbon-carbon bond cleavage furnished C-formyl alpha-l- and alpha-d-threofuranosides. The above C-glycosyl aldehydes were all prepared on a meaningful preparative scale starting from gram quantities of galactans. Finally, a new procedure for the preparation of the 2,3-O-benzyl l-threofuranose was established by Baeyer-Villiger oxidation of the benzylated C-formyl alpha-l-threofuranoside here prepared from agarose. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/19156325/Production_of_carbohydrate_building_blocks_from_red_seaweed_polysaccharides__Efficient_conversion_of_galactans_into_C_glycosyl_aldehydes_ L2 - https://doi.org/10.1039/b816606d DB - PRIME DP - Unbound Medicine ER -