Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors
D-Galactofuranose (D-Galf) is present in glycoconjugates of several pathogenic microorganisms but is absent in mammals, so it is a good target for the development of chemotherapeutic agents for the treatment of microbial infections. This fact has increased interest in the synthesis of D-Galf-contain...
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todo:paper_14394227_v15_n2_p189_Marino2023-10-03T16:16:14Z Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors Marino, C. Baldoni, L. carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis antiinfective agent carbohydrate derivative dextro galactofuranose derivative galactofuranosyl acceptor glycoconjugate oligosaccharide unclassified drug carbohydrate galactose polysaccharide carbohydrate synthesis drug synthesis glycobiology glycosylation linkage analysis nonhuman precursor priority journal review chemistry drug design galactofuranosides galactofuranosyl acceptors methodology organic synthesis synthesis Mammalia carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis Chemistry Techniques, Synthetic Drug Design Galactose Glycoconjugates Glycosylation Polysaccharides D-Galactofuranose (D-Galf) is present in glycoconjugates of several pathogenic microorganisms but is absent in mammals, so it is a good target for the development of chemotherapeutic agents for the treatment of microbial infections. This fact has increased interest in the synthesis of D-Galf-containing molecules for corresponding glycobiological studies. The synthesis of oligosaccharides, glycoconjugates, and mimetics of D-Galf requires specific methods for the preparation of galactose derivatives in the furanosic configuration, the synthesis of appropriate acceptors, and efficient glycosylation methods for the construction of α- and β-D-Galf linkages. This review summarizes the different strategies developed for the preparation of partially protected derivatives of D-Galf, suitable as acceptors for the construction of (1→2), (1→3), (1→5), and (1→6) link- ages, and describes recent applications. Three rings to rule them all: For the synthesis of D-Galf oligosaccharides and glycoconjugates, partially protected derivatives of D-galactofuranose that are suitable as glycosyl acceptors are synthesized mainly from three types of derivatives (type I, II, and III). This review describes the diverse strategies developed for this purpose and recent applications. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14394227_v15_n2_p189_Marino |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis antiinfective agent carbohydrate derivative dextro galactofuranose derivative galactofuranosyl acceptor glycoconjugate oligosaccharide unclassified drug carbohydrate galactose polysaccharide carbohydrate synthesis drug synthesis glycobiology glycosylation linkage analysis nonhuman precursor priority journal review chemistry drug design galactofuranosides galactofuranosyl acceptors methodology organic synthesis synthesis Mammalia carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis Chemistry Techniques, Synthetic Drug Design Galactose Glycoconjugates Glycosylation Polysaccharides |
| spellingShingle |
carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis antiinfective agent carbohydrate derivative dextro galactofuranose derivative galactofuranosyl acceptor glycoconjugate oligosaccharide unclassified drug carbohydrate galactose polysaccharide carbohydrate synthesis drug synthesis glycobiology glycosylation linkage analysis nonhuman precursor priority journal review chemistry drug design galactofuranosides galactofuranosyl acceptors methodology organic synthesis synthesis Mammalia carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis Chemistry Techniques, Synthetic Drug Design Galactose Glycoconjugates Glycosylation Polysaccharides Marino, C. Baldoni, L. Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| topic_facet |
carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis antiinfective agent carbohydrate derivative dextro galactofuranose derivative galactofuranosyl acceptor glycoconjugate oligosaccharide unclassified drug carbohydrate galactose polysaccharide carbohydrate synthesis drug synthesis glycobiology glycosylation linkage analysis nonhuman precursor priority journal review chemistry drug design galactofuranosides galactofuranosyl acceptors methodology organic synthesis synthesis Mammalia carbohydrates galactofuranosides galactofuranosyl acceptors glycosylation organic synthesis Chemistry Techniques, Synthetic Drug Design Galactose Glycoconjugates Glycosylation Polysaccharides |
| description |
D-Galactofuranose (D-Galf) is present in glycoconjugates of several pathogenic microorganisms but is absent in mammals, so it is a good target for the development of chemotherapeutic agents for the treatment of microbial infections. This fact has increased interest in the synthesis of D-Galf-containing molecules for corresponding glycobiological studies. The synthesis of oligosaccharides, glycoconjugates, and mimetics of D-Galf requires specific methods for the preparation of galactose derivatives in the furanosic configuration, the synthesis of appropriate acceptors, and efficient glycosylation methods for the construction of α- and β-D-Galf linkages. This review summarizes the different strategies developed for the preparation of partially protected derivatives of D-Galf, suitable as acceptors for the construction of (1→2), (1→3), (1→5), and (1→6) link- ages, and describes recent applications. Three rings to rule them all: For the synthesis of D-Galf oligosaccharides and glycoconjugates, partially protected derivatives of D-galactofuranose that are suitable as glycosyl acceptors are synthesized mainly from three types of derivatives (type I, II, and III). This review describes the diverse strategies developed for this purpose and recent applications. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| format |
JOUR |
| author |
Marino, C. Baldoni, L. |
| author_facet |
Marino, C. Baldoni, L. |
| author_sort |
Marino, C. |
| title |
Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| title_short |
Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| title_full |
Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| title_fullStr |
Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| title_full_unstemmed |
Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors |
| title_sort |
synthesis of d -galactofuranose-containing molecules: design of galactofuranosyl acceptors |
| url |
http://hdl.handle.net/20.500.12110/paper_14394227_v15_n2_p189_Marino |
| work_keys_str_mv |
AT marinoc synthesisofdgalactofuranosecontainingmoleculesdesignofgalactofuranosylacceptors AT baldonil synthesisofdgalactofuranosecontainingmoleculesdesignofgalactofuranosylacceptors |
| _version_ |
1807318275409838080 |