Preparation of C8-Amine and Acetylamine Adducts of 2‘-Deoxyguanosine Suitably Protected for DNA Synthesis

C8-Amine and acetylamine adducts of 2‘-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2‘-deoxyguanosine derivative, for the selective acetylation of the coupled adduct at N8 and for a protecting group scheme preserving the...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 24; pp. 4205 - 4208
Main Authors Gillet, Ludovic C. J, Schärer, Orlando D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.11.2002
Amer Chemical Soc
Subjects
Amines - chemical synthesis
Amines - chemistry
Chemistry
Chemistry, Organic
Deoxyguanosine - analogs & derivatives
Deoxyguanosine - chemical synthesis
DNA - chemical synthesis
Molecular Structure
Physical Sciences
Science & Technology
ACETYLAMINOFLUORENE
AMINATION
N-(2'-DEOXYGUANOSIN-8-YL)-2-(ACETYLAMINO)FLUORENE
RECOGNITION
BOND FORMATION
2'-DEOXYADENOSINE
DEPROTECTION
NUCLEOTIDE EXCISION-REPAIR
GENERAL-METHOD
OLIGONUCLEOTIDES
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Summary:C8-Amine and acetylamine adducts of 2‘-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2‘-deoxyguanosine derivative, for the selective acetylation of the coupled adduct at N8 and for a protecting group scheme preserving the integrity of the base-labile N8 acetyl group during DNA synthesis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol026474f