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Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

ABSTRACT: The first automated solution-phase synthesis of β-1,4-mannuronate and β-1,4-mannan oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, β-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the β-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to β-mannan synthesis.

SUBMITTER: Tang SL

PROVIDER: S-EPMC4460921 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

Tang Shu-Lun SL Pohl Nicola L B NL

Organic letters 20150508 11

The first automated solution-phase synthesis of β-1,4-mannuronate and β-1,4-mannan oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, β-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the β-1,4- ...[more]

PMID: 25955886

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