Synthesis and conformational properties of O-β -D-ribofuranosyl-(1″-2′)-guanosine and (adenosine)-5″ -phosphate

Article abstract of DOI:10.1081/NCN-120022748

The efficient synthesis of Grp and Arp, minor tRNA components, has been developed.

Full text of DOI:10.1081/NCN-120022748

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Synthesis and Conformational Properties of O-β-D-
Ribofuranosyl-(1″-2′)-guanosine and (Adenosine)-5″-
phosphate
Ekaterina V. Efimtseva a c , Alexandra A. Shelkunova a , Sergey N. Mikhailov a , Koen
Nauwelaerts b , Jef Rozenski b , Eveline Lescrinier b & Piet Herdewijn b
a Engelhardt Institute of Molecular Biology , Russian Academy of Sciences , Moscow, Russia
b Rega Institute , Katholieke Universiteit Leuven , Leuven, Belgium
c Engelhardt Institute of Molecular Biology , Russian Academy of Sciences , Vavilov str. 32,
119991, Moscow, Russia
Published online: 31 Aug 2006.
To cite this article: Ekaterina V. Efimtseva , Alexandra A. Shelkunova , Sergey N. Mikhailov , Koen Nauwelaerts , Jef
Rozenski , Eveline Lescrinier & Piet Herdewijn (2003) Synthesis and Conformational Properties of O-β-D-Ribofuranosyl-(1″-2′)-
guanosine and (Adenosine)-5″-phosphate, Nucleosides, Nucleotides and Nucleic Acids, 22:5-8, 1109-1111, DOI: 10.1081/
NCN-120022748
To link to this article: http://dx.doi.org/10.1081/NCN-120022748
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NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS
Vol. 22, Nos. 5–8, pp. 1109–1111, 2003
Synthesis and Conformational Properties of
O-b-D-Ribofuranosyl-(100-20)-guanosine
and (Adenosine)-500-phosphate
1
Ekaterina V. Efimtseva,1, Alexandra A. Shelkunova,
*
Sergey N. Mikhailov,1 Koen Nauwelaerts,2
Jef Rozenski,2 Eveline Lescrinier,2
and Piet Herdewijn2
1Engelhardt Institute of Molecular Biology, Russian Academy of Sciences,
Moscow, Russia
2Rega Institute, Katholieke Universiteit Leuven, Leuven, Belgium
ABSTRACT
The efficient synthesis of Grp and Arp, minor tRNA components, has been
developed.
Key Words: Minor tRNA components; Chemical synthesis; Phosphorylation.
Nucleic acids consist of over 100 modified nucleosides, in addition to 8 major
ribo- and deoxyribonucleosides. Although a few modifications have been found in
DNA, 81 modified nucleosides were found in tRNA’s and 15 were found in other
*Correspondence: Ekaterina V. Efimtseva, Engelhardt Institute of Molecular Biology,
Russian Academy of Sciences, Vavilov str. 32, 119991 Moscow, Russia; Fax: þ7 095 135
1405; E-mail: smikh@imb.ac.ru.
1109
DOI: 10.1081/NCN-120022748
Copyright # 2003 by Marcel Dekker, Inc.
1525-7770 (Print); 1532-2335 (Online)
www.dekker.com

1110
Efimtseva et al.
RNA’s. Most of the minor ribonucleosides have modified heterocyclic bases. Only
two types of sugar-modified nucleosides were found in RNA, namely 20-O-methyl
and 20-O-b-d-ribofuranosyl derivatives. The last derivatives, Grp and Arp (7a,b),
were isolated from initiator tRNAs of yeasts.[1]
The selective blocking of five hydroxyl groups in 20-O-b-d-ribofuranosylnucleo-
sides is an essential strategy in the preparation of the title compounds. Condensation
of 2 with 1a,b according to the earlier developed method[2] gave fully protected 3a,b.
Selective deblocking of phenoxyacetyl group was achieved in 0.1 M K2CO3 in
MeOH. The overall yields for the preparation of 4a,b were 46% and 38%, respec-
tively, higher then the earlier preparation of 4b (26%).[3] Further phosphorylation
gave 5a,b, after complete deblocking 7a,b were prepared in high overall yield
(18–20%).[4]
According to the NMR studies and molecular modeling these molecules are
rather flexible and show free rotation around the O- and N-glycosidic bonds.
a. SnCl4=ClCH2CH2Cl, 0ꢀC; b. 0.1 M K2CO3 in MeOH; c. bis(p-nitrophenylethyl)-
phosphate= TPSCl=1-methylimidazole=Py; d. Bu4NF=THF; e. DBU=Py; f. NH3=MeOH.

O-b-D-Ribofuranosyl-(100-20)-guanosine-500-phosphate
1111
ACKNOWLEDGMENT
Authors thank KUL Research Council and RFBR for financial support.
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4. Efimtseva, E.V.; Shelkunova, A.A.; Mikhailov, S.N.; Nauwelaerts, K.;
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ribofuranosyl-(100-20)-guanosine-500-O-phosphate and its derivatives. Helv. Chim.
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