NUCLEOSIDES .36. SYNTHESIS OF 3'-HOMOCITRULLYLAMINO-3-DEOXYADENOSINE AND 3'-LYSYLAMINO-3'-DEOXYADENOSINE AND THEIR RELATION TO CORDYCEPS-MILITARIS DERIVED PRODUCTS

被引:17
作者
LICHTENTHALER, FW
CUNY, E
MORINO, T
RYCHLIK, I
机构
[1] Institut für Organische Chemie und Biochemie, Technischen Hochschule Darmstadt, Darmstadt, D-6100
来源
CHEMISCHE BERICHTE-RECUEIL | 1979年 / 112卷 / 07期
关键词
D O I
10.1002/cber.19791120727
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Syntheses of N6‐desmethylpuromycin (6), of 3′‐L‐homocitrullylamino‐3′‐deoxyadenosine (3) and its L‐lysyl analog 4 are reported, based on a preparatively efficient procedure for the preparation of 3′‐amino‐3′‐deoxyadenosine (2) from D‐xylose, and on attachment of the corresponding amino acid components via the N‐benzyloxycarbonyl‐blocked N ‐hydroxysuccinimidyl and p‐nitrophenyl derivatives Z,Z‐Lys‐OSU (18), Z‐Phe(OMe)‐OSU (20) and Z‐hCit‐ONP (23), each characterized in crystalline form. – Synthetic 3 was identical with the product isolated previously from Cordyceps militaris, thus now unequivocally establishing its structure. – In biological evaluation, 3 and 4 exhibited inhibition of poly (U) directed polyphenylalanine synthesis analogous to that of puromycin (5), yet lower by factors of 20 and 40, respectively, whilst that of 6 was identical with 5 qualitatively and quantitatively; hence, the N6‐methyl groups in 5 are not essential for termination of ribosomal peptide chain elongation. Copyright © 1979 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
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页码:2588 / 2601
页数:14
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