PMID: 11931616Apr 5, 2002Paper

Bioactive pseudopeptidic analogues and cyclostereoisomers of osteogenic growth peptide C-terminal pentapeptide, OGP(10-14)

Journal of Medicinal Chemistry
Yu-Chen ChenMichael Chorev

Abstract

The osteogenic growth peptide (OGP) is a key factor in the mechanism of the systemic osteogenic response to local bone marrow injury. When administered in vivo, OGP stimulates osteogenesis and hematopoiesis. The C-terminal pentapeptide OGP(10-14) is the minimal amino acid sequence that retains the full OGP-like activity. Apparently, it is also the physiologic active form of OGP. Residues Tyr(10), Phe(12), Gly(13), and Gly(14) of OGP are essential for the OGP(10-14) activity. The present study explored the functional role of the peptide bonds, carboxyl and amino terminal groups, and conformational freedom in OGP(10-14). Transformations replacing the peptide bonds with surrogates such as Psi(CH(2)NH), Psi(CONMe), and Psi(CH(2)CH(2)) demonstrated that amide bonds do not contribute significantly to OGP(10-14) bioactivity. End-to-end cyclization yielded the fully bioactive cyclic pentapeptide c(Tyr-Gly-Phe-Gly-Gly). The retroinverso analogue c(Gly-Gly-phe-Gly-tyr), a cyclostereoisomer of c(Tyr-Gly-Phe-Gly-Gly), is at least as potent as the parent cyclic pentapeptide. The unique structure-activity relations revealed in this study suggest that the spatial presentation of the Tyr and Phe side chains has a major role in the productive i...Continue Reading

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Citations

Jun 15, 2016·Medicinal Research Reviews·Zaid AmsoMargaret A Brimble
Sep 24, 2015·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Gina M Policastro, Matthew L Becker
Aug 27, 2016·Carbohydrate Polymers·Hélida Gomes de Oliveira BarudSidney J L Ribeiro
Nov 24, 2016·International Journal of Molecular Sciences·Suzane C PigossiRaquel M Scarel-Caminaga
May 5, 2007·Angewandte Chemie·Franziska Mende, Oliver Seitz
Nov 20, 2016·Angewandte Chemie·Stefan J McCarverDavid W C MacMillan
May 27, 2011·The Journal of Organic Chemistry·Luke Hunter, Jonathan H Chung
Sep 25, 2021·Chemical Reviews·Lisa CandishSebastian Keess

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