TOPOCHEMICALLY RELATED HORMONE STRUCTURES: Synthesis of Partial Retro‐Inverso Analogs of LH‐RH
- 12 January 1981
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 17 (1) , 72-88
- https://doi.org/10.1111/j.1399-3011.1981.tb01970.x
Abstract
The syntheses of partial retro-inverso luteinizing hormone-releasing hormone [luliberin] (LH-RH) analogs, [g-Tyr5, m-Gly6]LH-RH, [g-Tyr5-r-Gly6, R,S-m-Leu7]LH-RH, [g-p-Glu1, m-His2]LH-RH, [g-p-Glu1-r-D-His-R,S-m-Trp3]LH-RH, and [g-Pro9-propionyl-des-Gly10]LH-RH, were accomplished by solution methods. The choice of sequence to be reversed was based on suggested biodegradation mechanisms of LH-RH. A (gem)-diamino alkylidene residue, which was produced via Curtius rearrangement of a peptide segment, and a 2-substituted malonyl residue mark the initiating and terminating site, respectively, of the reversed sequence.Keywords
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