Synthesis of a pair of novel receptors and their properties of enantioselective recognition for amino acid zwitterions

A pair of artificial enantiotopic receptors la and lb composed of (S,S) or (R,R) chiral bicyclic guanidinium, azacrown ether and (t-butyldiphenylsilyloxy) methyl group for amino acid zwitterions have been synthesized. The liquid-liquid competition experiments and 1 H NMR studies indicate that the receptor 1a with (S, S) configuration and 1b with (R,R) configuration selectively recognize L- and D-aromatic amino acids & respectively.

[1]  A. J. Kirby,et al.  Enzyme Mechanisms, Models, and Mimics , 1996 .

[2]  A. Hamilton,et al.  Acceleration of a Phosphate Diester Transesterification Reaction by Bis(alkylguanidinium) Receptors Containing an Appended General Base , 1995 .

[3]  P. Dervan,et al.  Recognition in the Minor Groove of DNA at 5'-(A,T)GCGC(A,T)-3' by a Four Ring Tripeptide Dimer. Reversal of the Specificity of the Natural Product Distamycin , 1995 .

[4]  A. Chamberlin,et al.  Enantioselective and Diastereoselective Molecular Recognition of Cyclic Dipeptides by a C2 Macrolactam Host , 1994 .

[5]  Julius Rebek,et al.  Water-Soluble Receptors for Cyclic-AMP and Their Use for Evaluating Phosphate-Guanidinium Interactions , 1994 .

[6]  S. Shinkai,et al.  Chiral Recognition of α-Amino Acid Derivatives by a Steroidal Crown Ether at the Air-Water Interface , 1994 .

[7]  Takuzo Aida,et al.  A novel anion-binding chiral receptor based on a metalloporphyrin with molecular asymmetry. Highly enantioselective recognition of amino acid derivatives , 1994 .

[8]  G. Gokel,et al.  Hydrogen bonding in macrocyclic receptor systems , 1993 .

[9]  David Andreu,et al.  A receptor for the enantioselective recognition of phenylalanine and tryptophan under neutral conditions , 1992 .

[10]  F. Schmidtchen,et al.  Abiotic anion receptor functions. A facile and dependable access to chiral guanidinium anchor groups , 1990 .

[11]  J. Lehn,et al.  Chiral recognition of aromatic carboxylate anions by an optically active abiotic receptor containing a rigid guanidinium binding subunit , 1989 .

[12]  P M Cullis,et al.  Affinities of amino acid side chains for solvent water. , 1981, Biochemistry.

[13]  D. Walba,et al.  HOST‐GUEST COMPLEXATION. 22. RECIPROCAL CHIRAL RECOGNITION BETWEEN AMINO ACIDS AND DILOCULAR SYSTEMS , 1980 .