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- Title
The Synthesis of [4-Carboranylalanine, 5-Leucine]-Enkephalin (Including an Improved Preparation of t-Butoxycarbonyl- L- o-carboranylalnine, New Derivatives of L-Propargylglycine, and a Note on Melanotropic and Opiate Receptor Binding Characteristics).
- Authors
Fauchère, Jean-Luc; Leukart, Othmar; Eberle, Alex; Schwyzer, Robert
- Abstract
The title compound, an analogue of [Leu5]-enkephalin with L- o-carboranylalanine replacing L-phenylalanine in position 4, was prepared by fragment condensation. The analogue has a 3-fold higher affinity for rat brain opiate receptors in the [3H]naloxone competition assay than natural [Leu5]-enkephalin. Like [Leu5]-enkephalin and Na-acetyl-[Leu5]-enkephalin, the N-terminal tripeptide fragment, H · Tyr-Gly-Gly · OH, had no melanotropic activity in the Rana pipiens frog skin assay. A convenient, direct synthesis of methyl t-butoxycarbonyl- L-propargylglycinate is described, and the 13C-NMR. spectra of L- o-carboranylalanine recorded. The procedure was extended to the preparation of BOC · Car-Leu · OMe from BOC · Pra-Leu · OMe. A number of new propargylglycine derivatives are reported.
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 5, p1385
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620502