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Complete NMR assignment and conformational analysis of 17‐ α ‐ethinylestradiol by using RDCs obtained in grafted graphene oxide
Author(s) -
França José A. A.,
NavarroVázquez Armando,
Lei Xinxiang,
Sun Han,
Griesinger Christian,
Hallwass Fernando
Publication year - 2017
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4526
Subject(s) - chemistry , graphene , oxide , ethinylestradiol , computational chemistry , combinatorial chemistry , nanotechnology , organic chemistry , materials science , population , demography , sociology , research methodology
The 1 H and 13 C NMR spectra of 17‐ α ‐ethinylestradiol ( EE2 ), a well‐known contraceptive, including diastereotopic methylene groups, were fully assigned with the help of residual dipolar couplings (RDC) measured in the recently developed grafted graphene oxide orienting medium. RDC analysis, which included all 1 D CH couplings and the long‐range 2 D CH 1 H―C≡ 13 C coupling, also pointed to the presence of a minor conformation arising from pseudo‐rotation of the steroid B ring. Saturation‐transfer difference (STD) measurements revealed that the most likely interaction between EE2 and orienting medium occurred on the C and D ring. Copyright © 2016 John Wiley & Sons, Ltd.