Original scientific paper

Aminoacyl Derivatives of 4-Thiothymidine, Cytosine, and Cytidine

V. Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, Zagreb, Croatia, Yugoslavia
G. Laćan ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, Zagreb, Croatia, Yugoslavia
Đ. Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, Zagreb, Croatia, Yugoslavia

Abstract

5'-0-Triphenylmerthyl-4-thiothymidine (III) was coupled to
N-benzyloxycarbonyl-D,L-alanine or N-t-butyloxycarbonyl-L-phenylalanine
by the N,N-dicyclohexylcarbodiimide method, yielding
3'-nucleos1de esters V and VII. The removal of the protectilng
triphenylmethyl and t-butyloxycarbonyl groups of compound VII
afforded 3'-0-(L-phenylalanyl)-4-thiothymidine (IX).
Appropriately blocked glycylglycine and L-phenyla1anine were
also coupled to cytosine and 2',3'-0-isopropylidene-cytidine by the
active ester or dicyclohexylcarbodiimide method, yie1ding N-4-
acylated cytosi1ne X and cytidine XIII. It was establi,shed that the
catalytic hydrogenation of 4-N-(glycylglycyl)-cytosine (XI) over
5°/o rhodium on carbon afforded 4-N-(glycylglycyl)-5,6-dihydrocytosine
(XII) in a quantitative yield.

Keywords

Hrčak ID:

196466

URI

https://hrcak.srce.hr/196466

Publication date:

23.9.1976.

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