Chemoenzymatic synthesis of C-4'-Spiro-oxetanoribonucleosides

Vivek Sharma; Manish Kumar; Deepti Sharma; Carl Erik Olsen; Ashok K. Prasad

doi:10.1021/jo501655j

Chemoenzymatic synthesis of C-4^'-Spiro-oxetanoribonucleosides

Vivek Sharma, Manish Kumar, Deepti Sharma, Carl Erik Olsen, Ashok K. Prasad

Section for Plant Biochemistry

13 Citations (Scopus)

Abstract

Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.

Original language	English
Journal	Journal of Organic Chemistry
Volume	79
Issue number	18
Pages (from-to)	8516-8521
Number of pages	6
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo501655j
Publication status	Published - 19 Sept 2014

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@article{6ce804fc27fe4ac9a26537aa75d8ff90,

title = "Chemoenzymatic synthesis of C-4'-Spiro-oxetanoribonucleosides",

abstract = "Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.",

author = "Vivek Sharma and Manish Kumar and Deepti Sharma and Olsen, {Carl Erik} and Prasad, {Ashok K.}",

year = "2014",

month = sep,

day = "19",

doi = "10.1021/jo501655j",

language = "English",

volume = "79",

pages = "8516--8521",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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TY - JOUR

T1 - Chemoenzymatic synthesis of C-4'-Spiro-oxetanoribonucleosides

AU - Sharma, Vivek

AU - Kumar, Manish

AU - Sharma, Deepti

AU - Olsen, Carl Erik

AU - Prasad, Ashok K.

PY - 2014/9/19

Y1 - 2014/9/19

N2 - Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.

AB - Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.

U2 - 10.1021/jo501655j

DO - 10.1021/jo501655j

M3 - Journal article

SN - 0022-3263

VL - 79

SP - 8516

EP - 8521

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Chemoenzymatic synthesis of C-4'-Spiro-oxetanoribonucleosides

Abstract

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Chemoenzymatic synthesis of C-4^'-Spiro-oxetanoribonucleosides