Chemo-enzymatic synthesis of 3-deoxy-β-D-ribofuranosyl purines and study of their biological properties

被引:8
|
作者
Barai, VN
Zinchenko, AI
Eroshevskaya, LA
Zhernosek, EV
Balzarini, J
De Clercq, E [1 ]
Mikhailopulo, IA
机构
[1] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
[2] Natl Acad Sci, Inst Microbiol, Minsk, BELARUS
[3] Natl Acad Sci, Inst Bioorgan Chem, Minsk, BELARUS
来源
关键词
enzymatic transglycosylation; purine nucleosides; activity;
D O I
10.1081/NCN-120022626
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
9-(3-Deoxy-beta-D-erythro-pentofuranosyl)-2,6-diiminopurine (2) was synthesized by an enzymatic transglycosylation of 2,6-diaminopurine using 3'-deoxycytidine (1) as a donor of the sugar moiety. Nucleoside 2 was transformed to 3'-deoxy guanosine (3), 9-(3-deoxy-beta-D-erythro-pentofuranosyl)-2-amino-6-oxopurine (3'-deoxyisoguanosine; 4), and 9-(3-deoxy-beta-D-erythro-pentofuranosyl)-2-fluoroadenine (5). Compounds 2-5 were evaluated for their anti-HIV activity.
引用
收藏
页码:751 / 753
页数:3
相关论文
共 50 条
  • [1] Chemo-enzymatic synthesis of 3-deoxy-β-D-ribofuranosyl purines
    Barai, VN
    Zinchenko, AI
    Eroshevskaya, LA
    Zhernosek, EV
    De Clercq, E
    Mikhailopulo, IA
    HELVETICA CHIMICA ACTA, 2002, 85 (07) : 1893 - 1900
  • [2] SYNTHESIS AND BIOLOGICAL EVALUATION OF 3-CHLORO-4-(D-RIBOFURANOSYL)-PYRIDINE AND 3-(D-RIBOFURANOSYL)-2-PYRIDONE
    BELMANS, M
    VRIJENS, I
    ESMANS, EL
    LEPOIVRE, JA
    ALDERWEIRELDT, FC
    WOTRING, LL
    TOWNSEND, LB
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1987, 6 (1-2): : 245 - 248
  • [3] Synthesis and physicochemical properties of 2′-deoxy-2',2"-difluoro-β-D-ribofuranosyl and 2′-deoxy-2′,2"-difluoro-α-D-ribofuranosyl oligonucleotides
    Viazovkina, E
    Mangos, MM
    Damha, MJ
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (5-8): : 1251 - 1254
  • [4] Convenient chemo-enzymatic synthesis of D-tagatose
    Freimund, S
    Huwig, A
    Giffhorn, F
    Kopper, S
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (01) : 115 - 120
  • [5] Convenient Chemo-Enzymatic Synthesis of D-Tagatose
    Freimund, S.
    Huwig, A.
    Giffhorn, F.
    Koepper, S.
    Journal of Carbohydrate Chemistry, 15 (01):
  • [6] Chemo-enzymatic synthesis and biological activity evaluation of propenylbenzene derivatives
    Hernik, Dawid
    Szczepanska, Ewa
    Ghezzi, Maria Chiara
    Brenna, Elisabetta
    Wloch, Aleksandra
    Pruchnik, Hanna
    Mularczyk, Malwina
    Marycz, Krzysztof
    Olejniczak, Teresa
    Boratynski, Filip
    FRONTIERS IN MICROBIOLOGY, 2023, 14
  • [7] Chemo-enzymatic synthesis of homogeneous hyaluronan polysaccharides and their biological applications
    Fang, Junqiang
    Wang, Peng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [8] A chemo-enzymatic approach to the study of carbohydrate recognition in biological systems
    Hendrix, M
    Wong, CH
    ENANTIOMER, 1996, 1 (4-6): : 305 - 310
  • [9] An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside
    Sultana, Israt
    Shimamoto, Miwa
    Obata, Rika
    Nishiyama, Shigeru
    Sugai, Takeshi
    SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS, 2006, 7 (02) : 197 - 201
  • [10] A Chemo-Enzymatic Synthesis of β-D-Arabinofuranosyl Purine Nucleosides
    Konstantinova, Irina D.
    Antonov, Konstantin V.
    Fateev, Ilja V.
    Miroshnikov, Anatoly I.
    Stepchenko, Vladimir A.
    Baranovsky, Alexander V.
    Mikhailopulo, Igor A.
    SYNTHESIS-STUTTGART, 2011, (10): : 1555 - 1560