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Volumn 51, Issue 33, 2010, Pages 4400-4402

Biocatalytic asymmetric formation of tetrahydro-β-carbolines

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; STRICTOSIDINE SYNTHASE; SYNTHETASE; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955424347     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.075     Document Type: Article
Times cited : (42)

References (27)
  • 20
    • 77955412460 scopus 로고    scopus 로고
    • note
    • +.
  • 21
    • 77955414169 scopus 로고    scopus 로고
    • note
    • Enantiomeric products derived from 4, 5, 7, and 8 were successfully separated (Supplementary data), but enantiomeric products derived from 6 could not be separated despite testing many chromatography conditions.
  • 24
    • 77955417303 scopus 로고    scopus 로고
    • note
    • Computational studies (11a) suggest the spiroindolenine intermediate is not a productive intermediate; attack from indole C2 to directly form 14 is the productive mechanism.
  • 25
    • 77955419975 scopus 로고    scopus 로고
    • note
    • Kinetic isotope effects suggest the Pictet-Spengler reaction is reversible prior to the final deprotonation step (11a).
  • 26
    • 77955430020 scopus 로고    scopus 로고
    • note
    • Point mutation of Phe226 (Figure 1B) to numerous ionizable residues did not impact the stereoselectivity of the reaction. More extensive mutagenesis of STS is underway to experimentally validate this hypothesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.