Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: different recognition of the anomers.

SABRINA IÑIGO, MARISA TAVERNA PORRO, JAVIER M. MONTSERRAT, LUIS E. IGLESIAS Y ADOLFO M. IRIBARREN

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

Elsevier

Lugar: London, New York; Año: 2005 vol. 35 p. 70 - 73

1381-1177

Abstract The anomers methyl 2,3,5-tri-O-acetyl--d-ribofuranoside and methyl 2,3,5-tri-O-acetyl--d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl 2,3-di-O-acetyl--d-ribofuranoside in 81% yield in 3 h at 45 .C showing no further transformation, the alcoholysis of the -diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the epimer, full deacetylated methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. . methyl -d-ribofuranoside was quantitatively formed at long reaction times (5 days). © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. © 2005 Elsevier B.V. All rights reserved. ..