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3α,3′α‐Bis( n ‐acetoxyphenylcarboxy)‐5β‐cholan‐24‐oic acid ethane‐1,2‐diol diesters ( n = 2–4): 13 C NMR chemical shifts, variable‐temperature and NOE 1 H NMR measurements and MO calculations of novel bile acid‐based dimers
Author(s) -
Tamminen Jari,
Kolehmainen Erkki,
Linnanto Juha,
Salo Hannu,
Mänttäri Pia
Publication year - 2000
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 - 10.1002/1097-458x(200010)38:10<877::aid-mrc750>3.0.co;2-2
Subject(s) - chemistry , lithocholic acid , diol , chemical shift , carbon 13 nmr , computational chemistry , stereochemistry , bile acid , organic chemistry , biochemistry
Three novel bile acid‐based molecular dimers, 3α,3′α‐bis( n ‐acetoxyphenylcarboxy)‐5β‐cholan‐24‐oic acid ethane‐1,2‐diol diesters ( n = 2–4), 1–3 , were synthesized from lithocholic acid (3α‐hydroxy‐5β‐cholan‐24‐oic acid) ethane‐1,2‐diol diester and isomeric n ‐acetoxybenzoyl chlorides ( n = 2–4). Their cleft type conformational preferences were suggested theoretically by PM3 molecular orbital calculations. Molecular weights determined by the matrix‐assisted laser desorption/ionization time‐of‐flight technique and 13 C NMR chemical shifts of the 1–3 are also presented. Copyright © 2000 John Wiley & Sons, Ltd.