Aminonucleosides and their derivatives. IV. Synthesis of the 3'-amino-3'-deoxynucleoside 5'-phosphates.

Nucleic acids research ·Vol. 6 ·No. 2 ·1979-02-00 ·Pages 625-43

Azhayev AV, Ozols AM, Bushnev AS, Dyatkina NB, Kochetkova SV, Victorova LS, Kukhanova MK, Krayevsky AA, Gottikh BP

Abstract

A new procedure has been developed for the synthesis of 3'-amino-3'-deoxyribonucleosides of adenine, cytosine and uracil by condensing the trimethylsilylated bases with peracylated 3-azido-3-deoxyribose derivative. The azido group could subsequently be reduced to amino. The 5'-phosphates of these nucleosides have been prepared and the analogues have been tested for their ability to stimulate the ribosome-catalyzed reaction of 3'(2')-O-(N-formylmethionyl) adenosine 5'-phosphate with phenylalanyl-tRNA.

MeSH Terms

Deoxyribonucleotides/chemical synthesis Electron Spin Resonance Spectroscopy Magnetic Resonance Spectroscopy Structure-Activity Relationship

Chemicals

Deoxyribonucleotides

Authors & Affiliations

9 authors, click to expand affiliations / ORCID

Azhayev A V

Ozols A M

Bushnev A S

Dyatkina N B

Kochetkova S V

Victorova L S

Kukhanova M K

Krayevsky A A

Gottikh B P

References (6)

6 references, click to expand

Preparation of a substituted 3-acetamido-3-deoxy-D-ribofuranosyl bromide suitable for the synthesis of puromycin analogs.
Carbohydr Res. 1975 May;41:318-22 PMID: 1137844
A novel procedure for the synthesis of 2'-O-alkyl nucleotides.
Biochemistry. 1972 Dec 19;11(26):4931-7 PMID: 4344474
Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants.
J Am Chem Soc. 1973 Apr 4;95(7):2333-44 PMID: 4709237
Effect of cytidine-5'-monophosphate on peptidyl transferase activity.
FEBS Lett. 1975 Oct 15;58(1):94-8 PMID: 1225607
Amino acids are not all initially attached to the same position on transfer RNA molecules.
Proc Natl Acad Sci U S A. 1975 Aug;72(8):3044-8 PMID: 1103136
A general synthesis of N-glycosides. 6. On the mechanism of the stannic chloride catalyzed silyl Hilbert-Johnson reaction.
J Org Chem. 1976 Jun 11;41(12):2084-6 PMID: 932850

Article Info

Journal

Nucleic acids research

Abbr.

Nucleic Acids Res

ISSN

0305-1048

DOI

10.1093/nar/6.2.625

Published

1979-02-00

Pages

625-43

Language

English

Region

England

NLM ID

0411011

PMCID

PMC327717

Subset

External Links

PubMed source DOI: 10.1093/nar/6.2.625 PMC Full Text View journal details

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Aminonucleosides and their derivatives. IV. Synthesis of the 3'-amino-3'-deoxynucleoside 5'-phosphates.

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