TY - JOUR
T1 - A simple efficient synthesis of [23,24]-13C2-labeled bile salts as NMR probes of protein-ligand interactions
AU - Tochtrop, Gregory P.
AU - DeKoster, Gregory T.
AU - Cistola, David P.
AU - Covey, Douglas F.
N1 - Funding Information:
This work was supported by PHS grants DK48046 and DK52574 to D.P.C. and GM 47969 to D.F.C.
PY - 2002/2/11
Y1 - 2002/2/11
N2 - The synthesis of [23,24]-13C2-labeled bile salts is achieved through a steroidal side chain degradation and isotopic regeneration strategy. Three common bile acids were degraded to the corresponding C22 aldehyde by an oxidative decarboxylation followed by ozonolysis. The side chain was subsequently regenerated via a Horner-Emmons reaction using an ylide generated from 13C2-labeled bromoacetic acid. These compounds were used as probes of protein-bile salt interactions using two- and three-dimensional NMR techniques.
AB - The synthesis of [23,24]-13C2-labeled bile salts is achieved through a steroidal side chain degradation and isotopic regeneration strategy. Three common bile acids were degraded to the corresponding C22 aldehyde by an oxidative decarboxylation followed by ozonolysis. The side chain was subsequently regenerated via a Horner-Emmons reaction using an ylide generated from 13C2-labeled bromoacetic acid. These compounds were used as probes of protein-bile salt interactions using two- and three-dimensional NMR techniques.
UR - http://www.scopus.com/inward/record.url?scp=0037059934&partnerID=8YFLogxK
U2 - 10.1016/S0960-894X(01)00763-6
DO - 10.1016/S0960-894X(01)00763-6
M3 - Article
C2 - 11814814
AN - SCOPUS:0037059934
SN - 0960-894X
VL - 12
SP - 433
EP - 435
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 3
ER -