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Long‐range 1 H‐ 15 N couplings and 15 N chemical shift assignments of the bis‐indole anticancer drug navelbine®
Author(s) -
Martin Gary E.,
Crouch Ronald C.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320627
Subject(s) - chemistry , heteronuclear molecule , indole test , vindoline , range (aeronautics) , stereochemistry , radiochemistry , nuclear magnetic resonance spectroscopy , composite material , medicine , materials science , vinblastine , surgery , chemotherapy
The recently reported application of gradient‐enhanced HMQC for the observation of long‐range 1 H‐ 15 N heteronuclear couplings at natural abundance has been extended to the bis‐indole anticancer drug Navelbine®. Responses correlating protons to N16′ (δ 15 N 138.2 ppm)in the velbanamine subunit and N1 and N9 (δ 15 N 66.0 and 55.3 ppm, respectively) in the vindoline subunit were observable within about 4 hours of data acquisition. The single response to N6′ (δ I5 N 43.0 ppm), in contrast, was very weak requiring a weekend data acquisition to even be observed. The difficulty in observing correlations to N6′ is presumably a function of molecular mobility in the eight‐membered azocine ring.