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

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 a...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 7; pp. 1928 - 1931
Main Authors Sawamoto, Hiroaki, Arai, Yuuki, Yamakoshi, Shuhei, Obika, Satoshi, Kawanishi, Eiji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2018
Amer Chemical Soc
Subjects
adenine
chemical structure
Chemistry
Chemistry, Organic
glycosylation
guanine
nucleic acids
Physical Sciences
Science & Technology
thymine
MONOMERS
5-METHYLCYTOSINE
AFFINITY
BRIDGED NUCLEIC-ACID
NUCLEOSIDES
THYMINE
ADENINE
OLIGODEOXYRIBONUCLEOTIDES
DERIVATIVES
OLIGONUCLEOTIDES
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.8b00476