TY - JOUR T1 - Expanding the structural repertoire of beta/alpha Ant-Pro (anthranilic acid-proline) oligomers into gamma/alpha 2-Amb-Pro (2-aminomethyl benzoic acid-proline) oligomers JF - Tetrahedron Y1 - 2012 A1 - Ramesh, Veera V. E. A1 - Priya, Gowri A1 - Rajamohanan, P. R. A1 - Hofmann, Hans-Joerg A1 - Sanjayan, Gangadhar J. KW - Amino acids KW - Foldamer KW - Peptides KW - Proline KW - Synthetic oligomers AB -

In this article, we report a novel class of heterogeneous synthetic oligomers featuring the conformationally constrained amino acid residues - 2-aminomethyl benzoic acid (2-Amb) and proline (Pro) in repeating sequences. Oligomers as large as hexadecamers featuring the conformationally restricted gamma/alpha 2-Amb-Pro motif have been assembled using solution-phase Boc strategy, following multi-step synthetic sequences starting from the commercially available O-toluic acid. EDC-mediated peptide coupling has been found to be optimum for the assembly of the relatively non-polar oligomers, which could be readily purified by the standard column chromatographic purification procedures. This study offers considerable prospects of expanding the structural repertoire of beta/alpha Ant-Pro motif, which has been described earlier to assume right-handed helical architecture displaying robust nine-membered-ring closed network of hydrogen-bonding interactions, into gamma/alpha 2-Amb-Pro motif. (C) 2012 Elsevier Ltd. All rights reserved.

PB - PERGAMON-ELSEVIER SCIENCE LTD CY - THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND VL - 68 IS - 23 U3 - Foreign U4 - 2.803 ER -