Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans
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 h...
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2003
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v338_n20_p2111_Navarro http://hdl.handle.net/20.500.12110/paper_00086215_v338_n20_p2111_Navarro |
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paper:paper_00086215_v338_n20_p2111_Navarro2023-06-08T14:32:44Z Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans Navarro, Diego Alberto Stortz, Carlos Arturo 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 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. Fil:Navarro, D.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2003 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v338_n20_p2111_Navarro http://hdl.handle.net/20.500.12110/paper_00086215_v338_n20_p2111_Navarro |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Navarro, Diego Alberto Stortz, Carlos Arturo Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| topic_facet |
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 |
| description |
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. |
| author |
Navarro, Diego Alberto Stortz, Carlos Arturo |
| author_facet |
Navarro, Diego Alberto Stortz, Carlos Arturo |
| author_sort |
Navarro, Diego Alberto |
| title |
Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| title_short |
Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| title_full |
Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| title_fullStr |
Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| title_full_unstemmed |
Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| title_sort |
determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans |
| publishDate |
2003 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v338_n20_p2111_Navarro http://hdl.handle.net/20.500.12110/paper_00086215_v338_n20_p2111_Navarro |
| work_keys_str_mv |
AT navarrodiegoalberto determinationoftheconfigurationof36anhydrogalactoseandcyclizableagalactose6sulfateunitsinredseaweedgalactans AT stortzcarlosarturo determinationoftheconfigurationof36anhydrogalactoseandcyclizableagalactose6sulfateunitsinredseaweedgalactans |
| _version_ |
1768543353705594880 |