Synthetic Method for 2′-Amino-LNA Bearing Any of the Four Nucleobases via a Transglycosylation Reaction

Hiroaki Sawamoto; Yuuki Arai; Shuhei Yamakoshi; Satoshi Obika; Eiji Kawanishi

doi:10.1021/acs.orglett.8b00476

Synthetic Method for 2′-Amino-LNA Bearing Any of the Four Nucleobases via a Transglycosylation Reaction

Hiroaki Sawamoto, Yuuki Arai, Shuhei Yamakoshi, Satoshi Obika, Eiji Kawanishi

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

A transglycosylation reaction of 2′-amino-locked nucleic acid (LNA) from thymine (T) to other nucleobases adenine (A), guanine (G), and 5-methylcytosine (^mC) has been developed. This reaction proceeds in high yield and with high β-selectivity. The mild reaction conditions enable the coexistence of acid-labile protecting groups, including a 4,4′-dimethoxytrytyl (DMTr) group. 2′-Amino-LNAs bearing any nucleobase can now be easily synthesized.

Original language	English
Pages (from-to)	1928-1931
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.8b00476
Publication status	Published - Apr 6 2018
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00476

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title = "Synthetic Method for 2′-Amino-LNA Bearing Any of the Four Nucleobases via a Transglycosylation Reaction",

abstract = "A transglycosylation reaction of 2′-amino-locked nucleic acid (LNA) from thymine (T) to other nucleobases adenine (A), guanine (G), and 5-methylcytosine (mC) has been developed. This reaction proceeds in high yield and with high β-selectivity. The mild reaction conditions enable the coexistence of acid-labile protecting groups, including a 4,4′-dimethoxytrytyl (DMTr) group. 2′-Amino-LNAs bearing any nucleobase can now be easily synthesized.",

author = "Hiroaki Sawamoto and Yuuki Arai and Shuhei Yamakoshi and Satoshi Obika and Eiji Kawanishi",

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T1 - Synthetic Method for 2′-Amino-LNA Bearing Any of the Four Nucleobases via a Transglycosylation Reaction

AU - Sawamoto, Hiroaki

AU - Arai, Yuuki

AU - Yamakoshi, Shuhei

AU - Obika, Satoshi

AU - Kawanishi, Eiji

PY - 2018/4/6

Y1 - 2018/4/6

N2 - A transglycosylation reaction of 2′-amino-locked nucleic acid (LNA) from thymine (T) to other nucleobases adenine (A), guanine (G), and 5-methylcytosine (mC) has been developed. This reaction proceeds in high yield and with high β-selectivity. The mild reaction conditions enable the coexistence of acid-labile protecting groups, including a 4,4′-dimethoxytrytyl (DMTr) group. 2′-Amino-LNAs bearing any nucleobase can now be easily synthesized.

AB - A transglycosylation reaction of 2′-amino-locked nucleic acid (LNA) from thymine (T) to other nucleobases adenine (A), guanine (G), and 5-methylcytosine (mC) has been developed. This reaction proceeds in high yield and with high β-selectivity. The mild reaction conditions enable the coexistence of acid-labile protecting groups, including a 4,4′-dimethoxytrytyl (DMTr) group. 2′-Amino-LNAs bearing any nucleobase can now be easily synthesized.

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JO - Organic letters

JF - Organic letters

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ER -

Synthetic Method for 2′-Amino-LNA Bearing Any of the Four Nucleobases via a Transglycosylation Reaction

Abstract

All Science Journal Classification (ASJC) codes

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