The influence of the purine 2-amino group on DNA conformation and stability-II. Synthesis and physical characterization of d[CGT(2-NH2)ACG], d[CGU(2-NH2)ACG], and d[CGT(2-NH2)AT(2-NH2)ACG]

Barbara L. Gaffney; Luis A. Marky; Roger A. Jones

doi:10.1016/0040-4020(84)85098-X

The influence of the purine 2-amino group on DNA conformation and stability-II. Synthesis and physical characterization of d[CGT(2-NH₂)ACG], d[CGU(2-NH₂)ACG], and d[CGT(2-NH₂)AT(2-NH₂)ACG]

Barbara L. Gaffney, Luis A. Marky, Roger A. Jones

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

107 Scopus citations

Abstract

Synthesis of an N-protected derivative of 2-amino-2'-deoxyadenosine (dA') from 2'-deoxyguanosine is reported. The syntheses of several oligodeoxynucleotides containing this modified nucleoside are described, together with physical characterization via melting studies and CD conformational analysis. As expected, the 2-amino group is seen to add to the duplex stability. Although the sequence d(TA')₃ was found to undergo a salt-induced conformational transition, mixed sequences such as d(CGTA'CG) did not display this behavior. All guanine residues present in these sequences were O⁶ protected, either with the cyanoethyl group or the 4-nitrophenylethyl group, to eliminate guanine degradation during phosphorylation and condensation reactions. Procedures for the introduction and removal of these O⁶ protecting groups are described.

Original language	English (US)
Pages (from-to)	3-13
Number of pages	11
Journal	Tetrahedron
Volume	40
Issue number	1
DOIs	https://doi.org/10.1016/0040-4020(84)85098-X
State	Published - 1984
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{cf4f48753e0f4eab95a2f6edcf5c6c2b,

title = "The influence of the purine 2-amino group on DNA conformation and stability-II. Synthesis and physical characterization of d[CGT(2-NH2)ACG], d[CGU(2-NH2)ACG], and d[CGT(2-NH2)AT(2-NH2)ACG]",

abstract = "Synthesis of an N-protected derivative of 2-amino-2'-deoxyadenosine (dA') from 2'-deoxyguanosine is reported. The syntheses of several oligodeoxynucleotides containing this modified nucleoside are described, together with physical characterization via melting studies and CD conformational analysis. As expected, the 2-amino group is seen to add to the duplex stability. Although the sequence d(TA')3 was found to undergo a salt-induced conformational transition, mixed sequences such as d(CGTA'CG) did not display this behavior. All guanine residues present in these sequences were O6 protected, either with the cyanoethyl group or the 4-nitrophenylethyl group, to eliminate guanine degradation during phosphorylation and condensation reactions. Procedures for the introduction and removal of these O6 protecting groups are described.",

author = "Gaffney, {Barbara L.} and Marky, {Luis A.} and Jones, {Roger A.}",

note = "Funding Information: Acknowledgments-The authorst hank S. Hadden and S. Kuxmich for excellenat nd enthusiasticte chnicaal ssistance and Dr. Kenneth J. Breslauerf or use of his laboratory facilities.T his work was supportedb y grants from the RutgersR esearchC ouncil, the BiomedicalR esearchS up port Grant, the AmericanC ancerS ociety( # CH-248),a nd the National Instituteso f Health (KJB; Grant GM 23509).",

year = "1984",

doi = "10.1016/0040-4020(84)85098-X",

language = "English (US)",

volume = "40",

pages = "3--13",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - The influence of the purine 2-amino group on DNA conformation and stability-II. Synthesis and physical characterization of d[CGT(2-NH2)ACG], d[CGU(2-NH2)ACG], and d[CGT(2-NH2)AT(2-NH2)ACG]

AU - Gaffney, Barbara L.

AU - Marky, Luis A.

AU - Jones, Roger A.

N1 - Funding Information: Acknowledgments-The authorst hank S. Hadden and S. Kuxmich for excellenat nd enthusiasticte chnicaal ssistance and Dr. Kenneth J. Breslauerf or use of his laboratory facilities.T his work was supportedb y grants from the RutgersR esearchC ouncil, the BiomedicalR esearchS up port Grant, the AmericanC ancerS ociety( # CH-248),a nd the National Instituteso f Health (KJB; Grant GM 23509).

PY - 1984

Y1 - 1984

N2 - Synthesis of an N-protected derivative of 2-amino-2'-deoxyadenosine (dA') from 2'-deoxyguanosine is reported. The syntheses of several oligodeoxynucleotides containing this modified nucleoside are described, together with physical characterization via melting studies and CD conformational analysis. As expected, the 2-amino group is seen to add to the duplex stability. Although the sequence d(TA')3 was found to undergo a salt-induced conformational transition, mixed sequences such as d(CGTA'CG) did not display this behavior. All guanine residues present in these sequences were O6 protected, either with the cyanoethyl group or the 4-nitrophenylethyl group, to eliminate guanine degradation during phosphorylation and condensation reactions. Procedures for the introduction and removal of these O6 protecting groups are described.

AB - Synthesis of an N-protected derivative of 2-amino-2'-deoxyadenosine (dA') from 2'-deoxyguanosine is reported. The syntheses of several oligodeoxynucleotides containing this modified nucleoside are described, together with physical characterization via melting studies and CD conformational analysis. As expected, the 2-amino group is seen to add to the duplex stability. Although the sequence d(TA')3 was found to undergo a salt-induced conformational transition, mixed sequences such as d(CGTA'CG) did not display this behavior. All guanine residues present in these sequences were O6 protected, either with the cyanoethyl group or the 4-nitrophenylethyl group, to eliminate guanine degradation during phosphorylation and condensation reactions. Procedures for the introduction and removal of these O6 protecting groups are described.

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U2 - 10.1016/0040-4020(84)85098-X

DO - 10.1016/0040-4020(84)85098-X

M3 - Article

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SN - 0040-4020

VL - 40

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EP - 13

JO - Tetrahedron

JF - Tetrahedron

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The influence of the purine 2-amino group on DNA conformation and stability-II. Synthesis and physical characterization of d[CGT(2-NH₂)ACG], d[CGU(2-NH₂)ACG], and d[CGT(2-NH₂)AT(2-NH₂)ACG]

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