Steroidal ureas as enantioselective receptors for an N-acetyl alpha-amino carboxylate.
[reaction: see text] Cholic acid has been elaborated into three regioisomeric bis-carbamoylureas, which have been investigated as enantioselective receptors for N-acetyl phenylalanine. L/D selectivities, peaking at 5:1, have been determined by a sensitive and rapid MS-based extraction method that should be generalizable to related systems.
Siracusa
Laura
L
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
Hurley
Fionn M
FM
Dresen
Stefan
S
Lawless
Laurence J
LJ
Pérez-Payán
M Nieves
MN
Davis
Anthony P
AP
D019826:Cholic Acid / Q000737:chemistry*; D018716:Molecular Mimicry; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D017459:Receptors, Amino Acid / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D014508:Urea / Q000737:chemistry
D017459:Receptors, Amino Acid; D012997:Solvents; D013256:Steroids; D010649:Phenylalanine; D014508:Urea; D019826:Cholic Acid; C044228:N-acetylphenylalanine