Synthesis and hybridization property of oligonucleotides containing carbocyclic oxetanocins

Shinobu Honzawa; Satoshi Ohwada; Yoshihiro Morishita; Kanae Sato; Nobuya Katagiri; Masahiko Yamaguchi

doi:10.1016/S0040-4020(00)00162-9

Synthesis and hybridization property of oligonucleotides containing carbocyclic oxetanocins

Shinobu Honzawa, Satoshi Ohwada, Yoshihiro Morishita, Kanae Sato, Nobuya Katagiri, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

1 Citation (Scopus)

Abstract

Oligonucleotides containing enantiomeric carbocyclic oxetanocins possessing adenine, thymine, guanine and cytosine were synthesized from an optically active cyclobutane derivative. Their hybridization properties with the complementary oligonucleotides were studied using melting point method, CD spectroscopy, and mixing curve method (Job plots). The artificial nucleotides possessing adenine, guanine and cytosine bases show tendency to form complexes more strongly with ribonucleotide than deoxyribonucleotide. These complexes are triplexes consisting of purine and pyrimidine in 1:2 ratio. Such triplex formation is observed both under high (1 M NaCl) and low salt conditions (0.1 M NaCl). (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2615-2627
Number of pages	13
Journal	Tetrahedron
Volume	56
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(00)00162-9
Publication status	Published - 2000 Apr 21

Keywords

Carbocyclic oxetanocins
Hybridization
Oligonucleotides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00162-9

Cite this

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title = "Synthesis and hybridization property of oligonucleotides containing carbocyclic oxetanocins",

abstract = "Oligonucleotides containing enantiomeric carbocyclic oxetanocins possessing adenine, thymine, guanine and cytosine were synthesized from an optically active cyclobutane derivative. Their hybridization properties with the complementary oligonucleotides were studied using melting point method, CD spectroscopy, and mixing curve method (Job plots). The artificial nucleotides possessing adenine, guanine and cytosine bases show tendency to form complexes more strongly with ribonucleotide than deoxyribonucleotide. These complexes are triplexes consisting of purine and pyrimidine in 1:2 ratio. Such triplex formation is observed both under high (1 M NaCl) and low salt conditions (0.1 M NaCl). (C) 2000 Elsevier Science Ltd.",

keywords = "Carbocyclic oxetanocins, Hybridization, Oligonucleotides",

author = "Shinobu Honzawa and Satoshi Ohwada and Yoshihiro Morishita and Kanae Sato and Nobuya Katagiri and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by the Terumo Science Foundation and Novartis Foundation (Japan) for the Promotion of Science.",

year = "2000",

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day = "21",

doi = "10.1016/S0040-4020(00)00162-9",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis and hybridization property of oligonucleotides containing carbocyclic oxetanocins

AU - Honzawa, Shinobu

AU - Ohwada, Satoshi

AU - Morishita, Yoshihiro

AU - Sato, Kanae

AU - Katagiri, Nobuya

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by the Terumo Science Foundation and Novartis Foundation (Japan) for the Promotion of Science.

PY - 2000/4/21

Y1 - 2000/4/21

N2 - Oligonucleotides containing enantiomeric carbocyclic oxetanocins possessing adenine, thymine, guanine and cytosine were synthesized from an optically active cyclobutane derivative. Their hybridization properties with the complementary oligonucleotides were studied using melting point method, CD spectroscopy, and mixing curve method (Job plots). The artificial nucleotides possessing adenine, guanine and cytosine bases show tendency to form complexes more strongly with ribonucleotide than deoxyribonucleotide. These complexes are triplexes consisting of purine and pyrimidine in 1:2 ratio. Such triplex formation is observed both under high (1 M NaCl) and low salt conditions (0.1 M NaCl). (C) 2000 Elsevier Science Ltd.

AB - Oligonucleotides containing enantiomeric carbocyclic oxetanocins possessing adenine, thymine, guanine and cytosine were synthesized from an optically active cyclobutane derivative. Their hybridization properties with the complementary oligonucleotides were studied using melting point method, CD spectroscopy, and mixing curve method (Job plots). The artificial nucleotides possessing adenine, guanine and cytosine bases show tendency to form complexes more strongly with ribonucleotide than deoxyribonucleotide. These complexes are triplexes consisting of purine and pyrimidine in 1:2 ratio. Such triplex formation is observed both under high (1 M NaCl) and low salt conditions (0.1 M NaCl). (C) 2000 Elsevier Science Ltd.

KW - Carbocyclic oxetanocins

KW - Hybridization

KW - Oligonucleotides

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UR - http://www.scopus.com/inward/citedby.url?scp=0034697294&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(00)00162-9

DO - 10.1016/S0040-4020(00)00162-9

M3 - Article

AN - SCOPUS:0034697294

SN - 0040-4020

VL - 56

SP - 2615

EP - 2627

JO - Tetrahedron

JF - Tetrahedron

IS - 17

ER -

Synthesis and hybridization property of oligonucleotides containing carbocyclic oxetanocins

Abstract

Keywords

ASJC Scopus subject areas

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