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Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta).
Carbohydr Res. 2007 Feb 26; 342(3-4):586-96.CR

Abstract

A polysaccharide fraction consisting of d-galactose, sulfate, and pyruvate in a molar proportion of 4:2:1 was isolated from the green seaweed Codium yezoense by water extraction followed by ion-exchange chromatography. To elucidate its structure, modified polysaccharides were prepared by desulfation, depyruvylation, and by total removal of non-carbohydrate substituents. Structures of the native polysaccharide and of the products of its chemical modifications were investigated by methylation analysis as well as by 1D and 2D (1)H and (13)C NMR spectroscopy. The polysaccharide devoid of sulfate and pyruvate was subjected to two subsequent Smith degradations to afford a rather low-molecular and essentially linear (1-->3)-beta-d-galactan. A highly ramified structure was suggested for the native polysaccharide, which contains linear backbone segments of 3-linked beta-d-galactopyranose residues connected by (1-->6) linkages, about 40% of 3-linked residues being additionally substituted at C-6, probably by short oligosaccharide residues also containing (1-->3) and (1-->6) linkages. Sulfate groups were found mainly at C-4 and in minor amounts at C-6. Pyruvate was found to form mainly five-membered cyclic ketals with O-3 and O-4 of the non-reducing terminal galactose residues. The minor part of pyruvate forms six-membered cyclic ketals with O-4 and O-6. The absolute configurations of ketals (R for six-membered ketals and S for five-membered ones) were established using NMR spectral data.

Authors+Show Affiliations

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii Prosp., 47, 119991 Moscow, Russian Federation.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17134684

Citation

Bilan, Maria I., et al. "Structure of a Highly Pyruvylated Galactan Sulfate From the Pacific Green Alga Codium Yezoense (Bryopsidales, Chlorophyta)." Carbohydrate Research, vol. 342, no. 3-4, 2007, pp. 586-96.
Bilan MI, Vinogradova EV, Shashkov AS, et al. Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta). Carbohydr Res. 2007;342(3-4):586-96.
Bilan, M. I., Vinogradova, E. V., Shashkov, A. S., & Usov, A. I. (2007). Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta). Carbohydrate Research, 342(3-4), 586-96.
Bilan MI, et al. Structure of a Highly Pyruvylated Galactan Sulfate From the Pacific Green Alga Codium Yezoense (Bryopsidales, Chlorophyta). Carbohydr Res. 2007 Feb 26;342(3-4):586-96. PubMed PMID: 17134684.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta). AU - Bilan,Maria I, AU - Vinogradova,Ekaterina V, AU - Shashkov,Alexander S, AU - Usov,Anatolii I, Y1 - 2006/11/12/ PY - 2006/08/11/received PY - 2006/10/31/revised PY - 2006/11/08/accepted PY - 2006/12/1/pubmed PY - 2007/4/17/medline PY - 2006/12/1/entrez SP - 586 EP - 96 JF - Carbohydrate research JO - Carbohydr Res VL - 342 IS - 3-4 N2 - A polysaccharide fraction consisting of d-galactose, sulfate, and pyruvate in a molar proportion of 4:2:1 was isolated from the green seaweed Codium yezoense by water extraction followed by ion-exchange chromatography. To elucidate its structure, modified polysaccharides were prepared by desulfation, depyruvylation, and by total removal of non-carbohydrate substituents. Structures of the native polysaccharide and of the products of its chemical modifications were investigated by methylation analysis as well as by 1D and 2D (1)H and (13)C NMR spectroscopy. The polysaccharide devoid of sulfate and pyruvate was subjected to two subsequent Smith degradations to afford a rather low-molecular and essentially linear (1-->3)-beta-d-galactan. A highly ramified structure was suggested for the native polysaccharide, which contains linear backbone segments of 3-linked beta-d-galactopyranose residues connected by (1-->6) linkages, about 40% of 3-linked residues being additionally substituted at C-6, probably by short oligosaccharide residues also containing (1-->3) and (1-->6) linkages. Sulfate groups were found mainly at C-4 and in minor amounts at C-6. Pyruvate was found to form mainly five-membered cyclic ketals with O-3 and O-4 of the non-reducing terminal galactose residues. The minor part of pyruvate forms six-membered cyclic ketals with O-4 and O-6. The absolute configurations of ketals (R for six-membered ketals and S for five-membered ones) were established using NMR spectral data. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/17134684/Structure_of_a_highly_pyruvylated_galactan_sulfate_from_the_Pacific_green_alga_Codium_yezoense__Bryopsidales_Chlorophyta__ DB - PRIME DP - Unbound Medicine ER -