Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

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

doi:10.1021/jo5008338

Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

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

Section for Plant Biochemistry

14 Citations (Scopus)

Abstract

Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

Original language	English
Journal	Journal of Organic Chemistry
Volume	79
Issue number	13
Pages (from-to)	6336-6341
Number of pages	6
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo5008338
Publication status	Published - 3 Jul 2014

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title = "Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides",

abstract = "Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.",

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

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T1 - Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

AU - Sharma, Vivek K.

AU - Kumar, Manish

AU - Olsen, Carl Erik

AU - Prasad, Ashok K.

PY - 2014/7/3

Y1 - 2014/7/3

N2 - Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

AB - Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

U2 - 10.1021/jo5008338

DO - 10.1021/jo5008338

M3 - Journal article

C2 - 24901539

SN - 0022-3263

VL - 79

SP - 6336

EP - 6341

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

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