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Volumn 53, Issue 33, 1997, Pages 11297-11306

Synthesis of (2'S,3'S)-9-(4'-phosphono-4',4'-difluoromethanobutyl)guanine and its enantiomer. Evaluation of the inhibitory activity for purine nucleoside phosphorylase

Author keywords

[No Author keywords available]

Indexed keywords

1 (DIETHOXYPHOSPHINYL)DIFLUOROMETHYL 2 HYDROXYMETHYLCYCLOPROPANE; 9 (4' PHOSPHONO 4',4' DIFLUORO 2',3' METHANOBUTYL)GUANINE; 9 (DIFLUOROPHOSPHONOPENTYL)GUANINE DERIVATIVE; GUANINE DERIVATIVE; PURINE NUCLEOSIDE PHOSPHORYLASE; PURINE NUCLEOSIDE PHOSPHORYLASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0030861194     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00704-7     Document Type: Article
Times cited : (31)

References (39)
  • 1
    • 0006131856 scopus 로고
    • Boyer, P. D., Ed.; Academic Press: New York
    • Parks, R. E., Jr.; Agarwal, R. P. In The Enzymes, 3rd ed.; Boyer, P. D., Ed.; Academic Press: New York, 1972; Vol. 7, pp 483-514.
    • (1972) The Enzymes, 3rd Ed. , vol.7 , pp. 483-514
    • Parks R.E., Jr.1    Agarwal, R.P.2
  • 15
    • 0342982555 scopus 로고
    • and refernces cited therein
    • Ouerfell, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Suda, M. Synthesis 1981, 714 and refernces cited therein.
    • (1981) , pp. 714
    • Suda, M.S.1
  • 16
    • 0343417899 scopus 로고    scopus 로고
    • note
    • Lipase AY did not catalyze the transesterification reaction.
  • 34
    • 0343417897 scopus 로고    scopus 로고
    • note
    • Theoretically, the transesterification having E = 12.3 should give (-)-6 with 94% ee in 40% yield when the reaction was terminated at the conversion of 60%. However, it was verified that the enzyme lost the activity during a long period to reach the conversion. Therefore, the second kinetic resolution was necessary to give (-)-6 with a high enantiomeric excess.
  • 36
    • 0343417896 scopus 로고    scopus 로고
    • note
    • Purchased from TOYOBO biochemicals.
  • 38
    • 0343417895 scopus 로고    scopus 로고
    • note
    • Among purine nuclosides, inosine was found to be the best substrate towards the PNP used in this study. The PNP is less reactive towards guanosine and adcnosine than inosine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.