Synthesis of conformationally constrained analogues of RGD tripeptide

Convergent syntheses of N-functionalized (3S,4S)-3-amino-4-vinyl-piperidin-2-one 10, trans-3-substituted proline 18 and (3S)-3-amino-piperidin-2-one 28 are developed. By incorporating these building blocks to an appropriate position, conformationally constrained analogues of RGD tripeptide (Arg-Gly-Asp) 2, 3 and 4 are designed and synthesized.

Graphical abstractDownload full-size imageConvergent syntheses of N-functionalized (3S,4S)-3-amino-4-vinyl-piperidin-2-one 10, trans-3-substituted proline 18 and (3S)-3-amino-piperidin-2-one 28 are developed. By incorporating these building blocks to an appropriate position, conformationally constrained analogues of RGD tripeptide Arg-Gly-Asp 2, 3 and 4 are designed and synthesized.