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Analysis of pyruvylated beta-carrageenan by 2D NMR spectroscopy and reductive partial hydrolysis.
Carbohydr Res. 2003 Jun 23; 338(13):1403-14.CR

Abstract

A polysaccharide rich in 4',6'-O-(1-carboxyethylidene)-substituted (i.e., pyruvylated) beta-carrageenan has been prepared by solvolytic desulfation of a polysaccharide containing predominantly pyruvylated alpha-carrageenan, which was extracted from the red seaweed, Callophycus tridentifer. The 13C and 1H NMR chemical shifts of pyruvylated beta-carrageenan have been fully assigned using 2D NMR spectroscopic techniques. The 4',6'-O-(1-methoxycarbonylethylidene) group, generated during chemical methylation of the polysaccharide, has been shown to survive under the conditions of acidic hydrolysis that cleave the 3,6-anhydro-alpha-D-galactosidic bonds in permethylated samples of both pyruvylated beta- and pyruvylated alpha-carrageenans. As a result, two novel pyruvylated carrabiitol derivatives have been prepared.

Authors+Show Affiliations

Falshaw R
Industrial Research Ltd, P.O. Box 31-310, Lower Hutt, New Zealand. r.falshaw@irl.cri.nz
Furneaux RH
No affiliation info available
Wong H
No affiliation info available

MeSH

CarrageenanGalactoseHydrolysisMolecular StructureMonosaccharidesNuclear Magnetic Resonance, BiomolecularPyruvic AcidRhodophytaXylitol

Pub Type(s)

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

Language

eng

PubMed ID

12801714

Citation

Falshaw, Ruth, et al. "Analysis of Pyruvylated Beta-carrageenan By 2D NMR Spectroscopy and Reductive Partial Hydrolysis." Carbohydrate Research, vol. 338, no. 13, 2003, pp. 1403-14.
Falshaw R, Furneaux RH, Wong H. Analysis of pyruvylated beta-carrageenan by 2D NMR spectroscopy and reductive partial hydrolysis. Carbohydr Res. 2003;338(13):1403-14.
Falshaw, R., Furneaux, R. H., & Wong, H. (2003). Analysis of pyruvylated beta-carrageenan by 2D NMR spectroscopy and reductive partial hydrolysis. Carbohydrate Research, 338(13), 1403-14.
Falshaw R, Furneaux RH, Wong H. Analysis of Pyruvylated Beta-carrageenan By 2D NMR Spectroscopy and Reductive Partial Hydrolysis. Carbohydr Res. 2003 Jun 23;338(13):1403-14. PubMed PMID: 12801714.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Analysis of pyruvylated beta-carrageenan by 2D NMR spectroscopy and reductive partial hydrolysis. AU - Falshaw,Ruth, AU - Furneaux,Richard H, AU - Wong,Herbert, PY - 2003/6/13/pubmed PY - 2004/5/5/medline PY - 2003/6/13/entrez SP - 1403 EP - 14 JF - Carbohydrate research JO - Carbohydr Res VL - 338 IS - 13 N2 - A polysaccharide rich in 4',6'-O-(1-carboxyethylidene)-substituted (i.e., pyruvylated) beta-carrageenan has been prepared by solvolytic desulfation of a polysaccharide containing predominantly pyruvylated alpha-carrageenan, which was extracted from the red seaweed, Callophycus tridentifer. The 13C and 1H NMR chemical shifts of pyruvylated beta-carrageenan have been fully assigned using 2D NMR spectroscopic techniques. The 4',6'-O-(1-methoxycarbonylethylidene) group, generated during chemical methylation of the polysaccharide, has been shown to survive under the conditions of acidic hydrolysis that cleave the 3,6-anhydro-alpha-D-galactosidic bonds in permethylated samples of both pyruvylated beta- and pyruvylated alpha-carrageenans. As a result, two novel pyruvylated carrabiitol derivatives have been prepared. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/12801714/Analysis_of_pyruvylated_beta_carrageenan_by_2D_NMR_spectroscopy_and_reductive_partial_hydrolysis_ DB - PRIME DP - Unbound Medicine ER -