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Synthesis of a beta-turn mimetic suitable for incorporation in the peptide hormone LHRH
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
2005 (English)In: TETRAHEDRON, ISSN 0040-4020, Vol. 61, no 21, 4901-9 p.Article in journal (Refereed) Published
Abstract [en]

LHRH is a decapeptide hormone which plays a central role in neuroendocrinology. Conformational studies have suggested that LHRH may adopt a beta-turn involving residues 5-8 when bound to its receptor. A beta-turn mimetic with side chains corresponding to those of a Tyr-Gly-Leu-Orn tetrapeptide has therefore been synthesized for incorporation at positions 5-8 in LHRH. In the turn mimetic, residues i and i + 1 are connected by a psi [CH2O] isostere instead of an amide bond, while a covalent ethylene bridge replaces the hydrogen bond which is often found between residues i and i+3 in beta-turns. The turn mimetic was assembled from three types of building blocks: an azido aldehyde, an Fmoc protected amino acid and a protected dipeptide amine.

Place, publisher, year, edition, pages
2005. Vol. 61, no 21, 4901-9 p.
Keyword [en]
peptidomimetic, beta-turn, LHRH, peptide hormone
Identifiers
URN: urn:nbn:se:umu:diva-13321DOI: doi:10.1016/j.tet.2005.03.061OAI: oai:DiVA.org:umu-13321DiVA: diva2:152992
Available from: 2007-05-08 Created: 2007-05-08 Last updated: 2011-01-12Bibliographically approved

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