Synthesis of (3R)-carboxy pyrrolidine (a β-proline analogue) and its oligomer

YJ Kim, DA Kaiser, TD Pollard, Y Ichikawa

Index: Kim, Yong Jip; Kaiser, Donald A.; Pollard, Thomas D.; Ichikawa, Yoshitaka Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 21 p. 2417 - 2419

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Citation Number: 18

Abstract

A decamer of a β-amino acid analogue of l-proline,(3R)-carboxy pyrrolidine (β-proline), was synthesized from a readily available (R)-glycidol. It was found to possess a rigid secondary structure, as evidenced by its CD spectrum. The β-proline decamer, however, failed to bind to profilin, whereas the corresponding α-l-proline decamer bound tightly to this protein.