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Abstract:

The enzymatic synthesis of a β-mannosyl (1 → 3) β-glucosyl (1 → 4) α-glucose-1-pyrophosphate-prenol (allylic) by Acetobacter xylinum preparations is described. Glucose pyrophosphate lipid, already known to be formed from UDP-glucose and endogenous phosphate lipid, is demonstrated to accept another glucose from UDP-glucose to give a cellobiose pyrophosphate lipid. The latter in turn accepts mannose from GDP-mannose to form a mannosyl cellobiose pyrophosphate lipid. The structure of the trisaccharide and the way it is linked to the lipid moiety were established by enzymatic and chemical methods such as mild alkaline and acid hydrolysis, phenol treatment, partial acid hydrolysis and acetolysis, periodate oxidation, borohydride reduction, and treatments with glycosidases. The α-unsaturated, polyprenolic nature of the lipid was inferred from and confirmed by the reaction between UDP-glucose and ficaprenol monophosphate to give glucose pyrophosphate ficaprenol, which had the same properties as the glucose pyrophosphate lipid formed from the endogenous acceptor. The allylic structure proposed for the endogenous acceptor is suggested by the lability to phenol treatment and catalytic reduction of its glycosylated derivatives. The enzyme preparation also synthesizes a β-mannose phosphate prenol (allylic), which does not seem to participate in the trisaccharide synthesis. The possible role of these sugar prenols in the synthesis of exopolysaccharides is considered. © 1980, All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum
Autor:Couso, R.O.; Ielpi, L.; García, R.C.; Dankert, M.A.
Filiación:Institute de Investigations Bioquímicas Fundación Campomar and Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Obligado 2490, Buenos Aires, 1428, Argentina
Palabras clave:mannosyl cellobiose diphosphate prenol; unclassified drug; guanosine diphosphate mannose; isoprenoid phosphate sugar; mannosylcellobiose diphosphate prenol; phenol derivative; uridine diphosphate glucose; animal experiment; Gluconacetobacter xylinus; in vitro study; Acetobacter; article; biosynthesis; chemistry; metabolism; oxidation reduction reaction; pH; Acetobacter; Animalia; Gluconacetobacter xylinus; Acetobacter; Chemistry; Guanosine Diphosphate Mannose; Hydrogen-Ion Concentration; Oxidation-Reduction; Phenols; Polyisoprenyl Phosphate Oligosaccharides; Polyisoprenyl Phosphate Sugars; Support, Non-U.S. Gov't; Support, U.S. Gov't, P.H.S.; Uridine Diphosphate Glucose
Año:1980
Volumen:204
Número:2
Página de inicio:434
Página de fin:443
DOI: http://dx.doi.org/10.1016/0003-9861(80)90054-5
Título revista:Archives of Biochemistry and Biophysics
Título revista abreviado:Arch. Biochem. Biophys.
ISSN:00039861
CAS:guanosine diphosphate mannose, 3123-67-9; uridine diphosphate glucose, 133-89-1; Guanosine Diphosphate Mannose, 3123-67-9; mannosylcellobiose diphosphate prenol; Phenols; Polyisoprenyl Phosphate Oligosaccharides; Polyisoprenyl Phosphate Sugars; Uridine Diphosphate Glucose, 133-89-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00039861_v204_n2_p434_Couso

Referencias:

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Citas:

---------- APA ----------
Couso, R.O., Ielpi, L., García, R.C. & Dankert, M.A. (1980) . Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum. Archives of Biochemistry and Biophysics, 204(2), 434-443.
http://dx.doi.org/10.1016/0003-9861(80)90054-5
---------- CHICAGO ----------
Couso, R.O., Ielpi, L., García, R.C., Dankert, M.A. "Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum" . Archives of Biochemistry and Biophysics 204, no. 2 (1980) : 434-443.
http://dx.doi.org/10.1016/0003-9861(80)90054-5
---------- MLA ----------
Couso, R.O., Ielpi, L., García, R.C., Dankert, M.A. "Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum" . Archives of Biochemistry and Biophysics, vol. 204, no. 2, 1980, pp. 434-443.
http://dx.doi.org/10.1016/0003-9861(80)90054-5
---------- VANCOUVER ----------
Couso, R.O., Ielpi, L., García, R.C., Dankert, M.A. Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum. Arch. Biochem. Biophys. 1980;204(2):434-443.
http://dx.doi.org/10.1016/0003-9861(80)90054-5