The hyperthermophilic member of family 1 of the glycosyl hydrolases, the b-glycosidase from the archaeon Sulfolobus solfataricus (Ssb-gly), has been used for an efficient synthesis of b-2-deoxyglucosides and for stereochemical studies of the reactions of glucal in the presence of alkyl and pyranosidic acceptors. Protonation of the double bond of glucal resulting in the equatorially disposed proton was observed and an indication of the protonating amino acid in the active site was obtained by the use of a mutant enzyme. The regioselectivity in the formation of b-2-deoxyglucosides of pyranosidic acceptors is different from that reported for mesophilic biocatalysts.

Enzymatic synthesis of 2-deoxy-β-glucosides and stereochemistry of β-glycosidase from Sulfolobus solfataricus on glucal / Trincone, Antonio; Pagnotta, Edoardo; Rossi, Mose'; Mazzone, Marialuisa; Moracci, Marco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 12:20(2001), pp. 2783-2787. [10.1016/S0957-4166(01)00491-8]

Enzymatic synthesis of 2-deoxy-β-glucosides and stereochemistry of β-glycosidase from Sulfolobus solfataricus on glucal

ROSSI, MOSE';MORACCI, Marco
2001

Abstract

The hyperthermophilic member of family 1 of the glycosyl hydrolases, the b-glycosidase from the archaeon Sulfolobus solfataricus (Ssb-gly), has been used for an efficient synthesis of b-2-deoxyglucosides and for stereochemical studies of the reactions of glucal in the presence of alkyl and pyranosidic acceptors. Protonation of the double bond of glucal resulting in the equatorially disposed proton was observed and an indication of the protonating amino acid in the active site was obtained by the use of a mutant enzyme. The regioselectivity in the formation of b-2-deoxyglucosides of pyranosidic acceptors is different from that reported for mesophilic biocatalysts.
2001
Enzymatic synthesis of 2-deoxy-β-glucosides and stereochemistry of β-glycosidase from Sulfolobus solfataricus on glucal / Trincone, Antonio; Pagnotta, Edoardo; Rossi, Mose'; Mazzone, Marialuisa; Moracci, Marco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 12:20(2001), pp. 2783-2787. [10.1016/S0957-4166(01)00491-8]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/673692
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 16
  • ???jsp.display-item.citation.isi??? 13
social impact