Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides
Abstract The levulinyl‐protected nucleosides are key building blocks for the solution‐phase synthesis of oligonucleotides. Short and efficient syntheses of 3′‐ and 5′‐ O ‐levulinylated 2′‐deoxyribonucleosides and 2′‐ O ‐methylribonucleosides have been developed from the corresponding nucleosides by...
Published in: | Current Protocols in Nucleic Acid Chemistry |
---|---|
Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2005
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/0471142700.nc0211s21 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2F0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/0471142700.nc0211s21 https://currentprotocols.onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 |
id |
crwiley:10.1002/0471142700.nc0211s21 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/0471142700.nc0211s21 2024-06-02T07:58:39+00:00 Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides Lavandera, Iván García, Javier Fernández, Susana Ferrero, Miguel Gotor, Vicente Sanghvi, Yogesh S. 2005 http://dx.doi.org/10.1002/0471142700.nc0211s21 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2F0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/0471142700.nc0211s21 https://currentprotocols.onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Current Protocols in Nucleic Acid Chemistry volume 21, issue 1 ISSN 1934-9270 1934-9289 journal-article 2005 crwiley https://doi.org/10.1002/0471142700.nc0211s21 2024-05-03T10:57:14Z Abstract The levulinyl‐protected nucleosides are key building blocks for the solution‐phase synthesis of oligonucleotides. Short and efficient syntheses of 3′‐ and 5′‐ O ‐levulinylated 2′‐deoxyribonucleosides and 2′‐ O ‐methylribonucleosides have been developed from the corresponding nucleosides by enzyme‐catalyzed regioselective acylation in organic solvents or from 3′,5′‐di‐ O ‐levulinyl derivatives by regioselective enzymatic hydrolysis. Lipase‐mediated levulinylation of various nucleosides has been accomplished with acetonoxime levulinate as an acyl donor. Use of immobilized Pseudomonas cepacia lipase (PSL‐C) has furnished 3′‐ O ‐levulinylated 2′‐deoxyribonucleosides in excellent yields. Similarly, Candida antarctica lipase B (CAL‐B) has provided 5′‐ O ‐levulinylated nucleosides in high yields. 3′‐ O ‐Levulinylated 2′‐deoxyribonucleosides and 2′‐ O ‐methylribonucleosides were prepared via selective hydrolysis of 3′,5′‐di‐ O ‐levulinate esters using CAL‐B. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Current Protocols in Nucleic Acid Chemistry 21 1 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract The levulinyl‐protected nucleosides are key building blocks for the solution‐phase synthesis of oligonucleotides. Short and efficient syntheses of 3′‐ and 5′‐ O ‐levulinylated 2′‐deoxyribonucleosides and 2′‐ O ‐methylribonucleosides have been developed from the corresponding nucleosides by enzyme‐catalyzed regioselective acylation in organic solvents or from 3′,5′‐di‐ O ‐levulinyl derivatives by regioselective enzymatic hydrolysis. Lipase‐mediated levulinylation of various nucleosides has been accomplished with acetonoxime levulinate as an acyl donor. Use of immobilized Pseudomonas cepacia lipase (PSL‐C) has furnished 3′‐ O ‐levulinylated 2′‐deoxyribonucleosides in excellent yields. Similarly, Candida antarctica lipase B (CAL‐B) has provided 5′‐ O ‐levulinylated nucleosides in high yields. 3′‐ O ‐Levulinylated 2′‐deoxyribonucleosides and 2′‐ O ‐methylribonucleosides were prepared via selective hydrolysis of 3′,5′‐di‐ O ‐levulinate esters using CAL‐B. |
format |
Article in Journal/Newspaper |
author |
Lavandera, Iván García, Javier Fernández, Susana Ferrero, Miguel Gotor, Vicente Sanghvi, Yogesh S. |
spellingShingle |
Lavandera, Iván García, Javier Fernández, Susana Ferrero, Miguel Gotor, Vicente Sanghvi, Yogesh S. Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
author_facet |
Lavandera, Iván García, Javier Fernández, Susana Ferrero, Miguel Gotor, Vicente Sanghvi, Yogesh S. |
author_sort |
Lavandera, Iván |
title |
Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
title_short |
Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
title_full |
Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
title_fullStr |
Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
title_full_unstemmed |
Enzymatic Regioselective Levulinylation of 2′‐Deoxyribonucleosides and 2′‐ O‐Methylribonucleosides |
title_sort |
enzymatic regioselective levulinylation of 2′‐deoxyribonucleosides and 2′‐ o‐methylribonucleosides |
publisher |
Wiley |
publishDate |
2005 |
url |
http://dx.doi.org/10.1002/0471142700.nc0211s21 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2F0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/0471142700.nc0211s21 https://currentprotocols.onlinelibrary.wiley.com/doi/pdf/10.1002/0471142700.nc0211s21 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Current Protocols in Nucleic Acid Chemistry volume 21, issue 1 ISSN 1934-9270 1934-9289 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/0471142700.nc0211s21 |
container_title |
Current Protocols in Nucleic Acid Chemistry |
container_volume |
21 |
container_issue |
1 |
_version_ |
1800742093347356672 |