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Abstract:

A combination of two reported procedures was used in order to determine the configuration of the 3,6-anhydrogalactose present in red seaweed polysaccharides. A mild hydrolysis (to cleave only 3,6-anhydrogalactosyl linkages) was followed by a reductive amination with a chiral amine. Then, the total hydrolysis proceeded, followed by a new step of reductive amination. In this way, using (S)-α-methylbenzylamine as the chiral amine, it was possible to separate and quantitate both enantiomers of 3,6-AnGal and its 2-O-methyl ether as their diastereomeric acetylated aminoalditols. On the other hand, using (S)-1-amino-2-propanol, even though the derivatives of both enantiomers of 3,6-AnGal are not separated, the mixture can be safely quantitated with respect to galactose. Furthermore, a one-pot technique was developed to carry out an alkaline treatment of the polysaccharides, followed by the double hydrolysis-reductive amination procedure, which is useful to determine the proportions of both enantiomers of 6-sulfated 4-linked galactose units in the native polysaccharides. The unexpected presence of small amounts of units of this type belonging to the D-series in a porphyran sample is revealed by this novel procedure. © 2003 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans
Autor:Navarro, D.A.; Stortz, C.A.
Filiación:Depto. de Quim. Organ.-CIHIDECAR, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:3,6-Anhydrogalactose; Agarans; Carrageenans; Enantiomers; Seaweed galactans; Alcohols; Amination; Hydrolysis; Sulfur compounds; Enantiomers; Carbohydrates; 3,6 anhydrogalactose; alcohol derivative; alditol; alpha galactose 6 sulfate; amine; dimethyl ether; galactan; galactose; polysaccharide; propanol; unclassified drug; amination; article; carbohydrate analysis; controlled study; diastereoisomer; enantiomer; hydrolysis; nonhuman; priority journal; seaweed; technique; algae
Año:2003
Volumen:338
Número:20
Página de inicio:2111
Página de fin:2118
DOI: http://dx.doi.org/10.1016/S0008-6215(03)00345-8
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:dimethyl ether, 115-10-6; galactan, 39300-87-3, 9037-55-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; propanol, 62309-51-7, 71-23-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v338_n20_p2111_Navarro

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Citas:

---------- APA ----------
Navarro, D.A. & Stortz, C.A. (2003) . Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans. Carbohydrate Research, 338(20), 2111-2118.
http://dx.doi.org/10.1016/S0008-6215(03)00345-8
---------- CHICAGO ----------
Navarro, D.A., Stortz, C.A. "Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans" . Carbohydrate Research 338, no. 20 (2003) : 2111-2118.
http://dx.doi.org/10.1016/S0008-6215(03)00345-8
---------- MLA ----------
Navarro, D.A., Stortz, C.A. "Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans" . Carbohydrate Research, vol. 338, no. 20, 2003, pp. 2111-2118.
http://dx.doi.org/10.1016/S0008-6215(03)00345-8
---------- VANCOUVER ----------
Navarro, D.A., Stortz, C.A. Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans. Carbohydr. Res. 2003;338(20):2111-2118.
http://dx.doi.org/10.1016/S0008-6215(03)00345-8