Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions

Cryptonemia seminervis biosynthesizes a family of d,l-hybrid galactans based on the classical 3-linked β-d-galactopyranosyl→4-linked α-d- and α-l-galactopyranosyl alternating sequence (A-units→B-units) with major amounts of α-d- and α-l-galactose and 3,6-anhydro-d- and l-galactose and lesser percent...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Zibetti, R.G.M., Duarte, M.E.R., Noseda, M.D., Colodi, F.G., Ducatti, D.R.B., Ferreira, L.G., Cardoso, M.A., Cerezo, A.S.
Formato: JOUR
Materias:
Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Polysaccharides
Red seaweed
Sulfated galactans
Biopolymers
Kinetic theory
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Organic acids
Rate constants
Seaweed
acetal
alpha galactosidase
carrageenan
galactan
galactose
monosaccharide
pyranoside
pyruvic acid
sulfate
article
biosynthesis
carbohydrate analysis
carbon nuclear magnetic resonance
chemical reaction
chemical structure
cryptonemia seminervis
cyclization
depolymerization
infrared spectroscopy
kinetics
methylation
nonhuman
priority journal
proton nuclear magnetic resonance
seaweed
Algae, Red
Galactans
Nuclear Magnetic Resonance, Biomolecular
Spectroscopy, Fourier Transform Infrared
Cryptonemia
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v344_n17_p2364_Zibetti
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00086215_v344_n17_p2364_Zibetti
record_format dspace
spelling todo:paper_00086215_v344_n17_p2364_Zibetti2023-10-03T14:07:20Z Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions Zibetti, R.G.M. Duarte, M.E.R. Noseda, M.D. Colodi, F.G. Ducatti, D.R.B. Ferreira, L.G. Cardoso, M.A. Cerezo, A.S. Cryptonemia seminervis Halymeniales NMR spectroscopy Polysaccharides Red seaweed Sulfated galactans Cryptonemia seminervis Halymeniales NMR spectroscopy Red seaweed Sulfated galactans Biopolymers Kinetic theory Nuclear magnetic resonance Nuclear magnetic resonance spectroscopy Organic acids Rate constants Seaweed Polysaccharides acetal alpha galactosidase carrageenan galactan galactose monosaccharide pyranoside pyruvic acid sulfate article biosynthesis carbohydrate analysis carbon nuclear magnetic resonance chemical reaction chemical structure cryptonemia seminervis cyclization depolymerization infrared spectroscopy kinetics methylation nonhuman priority journal proton nuclear magnetic resonance seaweed Algae, Red Galactans Nuclear Magnetic Resonance, Biomolecular Spectroscopy, Fourier Transform Infrared Cryptonemia Cryptonemia seminervis Halymeniales Cryptonemia seminervis biosynthesizes a family of d,l-hybrid galactans based on the classical 3-linked β-d-galactopyranosyl→4-linked α-d- and α-l-galactopyranosyl alternating sequence (A-units→B-units) with major amounts of α-d- and α-l-galactose and 3,6-anhydro-d- and l-galactose and lesser percentages of 3,6-anhydro-2-O-methyl-l-galactose, 2-O-methyl-, 4-O-methyl- and 6-O-methylgalactoses. The dispersion of structures in this family is based on five structural factors, namely: (a) the amount and position of substituent groups as sulfate (major), pyruvic acid ketals, methoxyl and glycosyl side-chain (4-O-methyl galactopyranosyl and/or xylosyl); (b) the ratio galactose/3,6-anhydrogalactose in the B-units; (c) the ratio d,l-galactoses and d,l-3,6-anhydrogalactoses also in the B-units, (d) the formation of diads and (e) the sequence of the diads in the linear backbone. Considering these variables it is not unexpected to find in the fractions studied at least 18 structural units producing highly complex structures. Structural studies carried out in two major fractions (S2S-3 and S2S-4) showed that these galactans were formed mainly by β-d-galactopyranosyl 2-sulfate (20 and 11.9 mol %), β-d-galactopyranosyl 2-sulfate 4,6-O-(1′-carboxyethylidene) (8.9 and 6.0 mol %) and β-d-galactopyranosyl 2,6-sulfate (5.4 and 18.6 mol %), together with 3,6-anhydro-α-l-galactopyranosyl (11.4 and 7.3 mol %) and 3,6-anhydro-α-l-galactopyranosyl 2-sulfate (4.9 and 15.4 mol %) and minor quantities of 12-15 other structural units. Preparative alkaline treatment carried out on fraction (S2S-3) produced a quantitative formation of 3,6-anhydro α-l-galactopyranosyl units from precursor units (α-l-galactose 6-sulfate and α-l-galactose 2,6-sulfate). Kinetic studies on this 3,6-anhydro cyclization show a rate constant of 5.2 × 104 s-1 indicating diads of the type G→L6S/2,6S. Data from chemical, spectroscopic and kinetic studies suggest that, in S2S-3, the agaran block in the d,l-hybrid galactan is composed of the following diads: G(6R)→L6S/2,6S and G2S(P)(2,6S)→LA(2S)(2R)(2M) and the carrageenan block of G2S(P)→D(2S)(2,3S)(3S)(3,6S) in a molar ratio of agaran to carrageenan structures of ∼2:1. © 2009 Elsevier Ltd. All rights reserved. Fil:Noseda, M.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cerezo, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v344_n17_p2364_Zibetti
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Polysaccharides
Red seaweed
Sulfated galactans
Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Red seaweed
Sulfated galactans
Biopolymers
Kinetic theory
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Organic acids
Rate constants
Seaweed
Polysaccharides
acetal
alpha galactosidase
carrageenan
galactan
galactose
monosaccharide
pyranoside
pyruvic acid
sulfate
article
biosynthesis
carbohydrate analysis
carbon nuclear magnetic resonance
chemical reaction
chemical structure
cryptonemia seminervis
cyclization
depolymerization
infrared spectroscopy
kinetics
methylation
nonhuman
priority journal
proton nuclear magnetic resonance
seaweed
Algae, Red
Galactans
Nuclear Magnetic Resonance, Biomolecular
Spectroscopy, Fourier Transform Infrared
Cryptonemia
Cryptonemia seminervis
Halymeniales
spellingShingle Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Polysaccharides
Red seaweed
Sulfated galactans
Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Red seaweed
Sulfated galactans
Biopolymers
Kinetic theory
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Organic acids
Rate constants
Seaweed
Polysaccharides
acetal
alpha galactosidase
carrageenan
galactan
galactose
monosaccharide
pyranoside
pyruvic acid
sulfate
article
biosynthesis
carbohydrate analysis
carbon nuclear magnetic resonance
chemical reaction
chemical structure
cryptonemia seminervis
cyclization
depolymerization
infrared spectroscopy
kinetics
methylation
nonhuman
priority journal
proton nuclear magnetic resonance
seaweed
Algae, Red
Galactans
Nuclear Magnetic Resonance, Biomolecular
Spectroscopy, Fourier Transform Infrared
Cryptonemia
Cryptonemia seminervis
Halymeniales
Zibetti, R.G.M.
Duarte, M.E.R.
Noseda, M.D.
Colodi, F.G.
Ducatti, D.R.B.
Ferreira, L.G.
Cardoso, M.A.
Cerezo, A.S.
Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
topic_facet Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Polysaccharides
Red seaweed
Sulfated galactans
Cryptonemia seminervis
Halymeniales
NMR spectroscopy
Red seaweed
Sulfated galactans
Biopolymers
Kinetic theory
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Organic acids
Rate constants
Seaweed
Polysaccharides
acetal
alpha galactosidase
carrageenan
galactan
galactose
monosaccharide
pyranoside
pyruvic acid
sulfate
article
biosynthesis
carbohydrate analysis
carbon nuclear magnetic resonance
chemical reaction
chemical structure
cryptonemia seminervis
cyclization
depolymerization
infrared spectroscopy
kinetics
methylation
nonhuman
priority journal
proton nuclear magnetic resonance
seaweed
Algae, Red
Galactans
Nuclear Magnetic Resonance, Biomolecular
Spectroscopy, Fourier Transform Infrared
Cryptonemia
Cryptonemia seminervis
Halymeniales
description Cryptonemia seminervis biosynthesizes a family of d,l-hybrid galactans based on the classical 3-linked β-d-galactopyranosyl→4-linked α-d- and α-l-galactopyranosyl alternating sequence (A-units→B-units) with major amounts of α-d- and α-l-galactose and 3,6-anhydro-d- and l-galactose and lesser percentages of 3,6-anhydro-2-O-methyl-l-galactose, 2-O-methyl-, 4-O-methyl- and 6-O-methylgalactoses. The dispersion of structures in this family is based on five structural factors, namely: (a) the amount and position of substituent groups as sulfate (major), pyruvic acid ketals, methoxyl and glycosyl side-chain (4-O-methyl galactopyranosyl and/or xylosyl); (b) the ratio galactose/3,6-anhydrogalactose in the B-units; (c) the ratio d,l-galactoses and d,l-3,6-anhydrogalactoses also in the B-units, (d) the formation of diads and (e) the sequence of the diads in the linear backbone. Considering these variables it is not unexpected to find in the fractions studied at least 18 structural units producing highly complex structures. Structural studies carried out in two major fractions (S2S-3 and S2S-4) showed that these galactans were formed mainly by β-d-galactopyranosyl 2-sulfate (20 and 11.9 mol %), β-d-galactopyranosyl 2-sulfate 4,6-O-(1′-carboxyethylidene) (8.9 and 6.0 mol %) and β-d-galactopyranosyl 2,6-sulfate (5.4 and 18.6 mol %), together with 3,6-anhydro-α-l-galactopyranosyl (11.4 and 7.3 mol %) and 3,6-anhydro-α-l-galactopyranosyl 2-sulfate (4.9 and 15.4 mol %) and minor quantities of 12-15 other structural units. Preparative alkaline treatment carried out on fraction (S2S-3) produced a quantitative formation of 3,6-anhydro α-l-galactopyranosyl units from precursor units (α-l-galactose 6-sulfate and α-l-galactose 2,6-sulfate). Kinetic studies on this 3,6-anhydro cyclization show a rate constant of 5.2 × 104 s-1 indicating diads of the type G→L6S/2,6S. Data from chemical, spectroscopic and kinetic studies suggest that, in S2S-3, the agaran block in the d,l-hybrid galactan is composed of the following diads: G(6R)→L6S/2,6S and G2S(P)(2,6S)→LA(2S)(2R)(2M) and the carrageenan block of G2S(P)→D(2S)(2,3S)(3S)(3,6S) in a molar ratio of agaran to carrageenan structures of ∼2:1. © 2009 Elsevier Ltd. All rights reserved.
format JOUR
author Zibetti, R.G.M.
Duarte, M.E.R.
Noseda, M.D.
Colodi, F.G.
Ducatti, D.R.B.
Ferreira, L.G.
Cardoso, M.A.
Cerezo, A.S.
author_facet Zibetti, R.G.M.
Duarte, M.E.R.
Noseda, M.D.
Colodi, F.G.
Ducatti, D.R.B.
Ferreira, L.G.
Cardoso, M.A.
Cerezo, A.S.
author_sort Zibetti, R.G.M.
title Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
title_short Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
title_full Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
title_fullStr Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
title_full_unstemmed Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
title_sort galactans from cryptonemia species. part ii: studies on the system of galactans of cryptonemia seminervis (halymeniales) and on the structure of major fractions
url http://hdl.handle.net/20.500.12110/paper_00086215_v344_n17_p2364_Zibetti
work_keys_str_mv AT zibettirgm galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT duartemer galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT nosedamd galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT colodifg galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT ducattidrb galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT ferreiralg galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT cardosoma galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
AT cerezoas galactansfromcryptonemiaspeciespartiistudiesonthesystemofgalactansofcryptonemiaseminervishalymenialesandonthestructureofmajorfractions
_version_ 1782023771138293760

Ejemplares similares