Synthetische Analoge des Hypertensins. IV. Synthese der kettenhomologen Peptide (des-Asp1)-Val5-Hypertensin II, (des-Phe8)-Val5-Hypertensin II-Asp1-β-amid, (homo-Tyr4′)-Val5-Hypertensin II und (homo-Tyr4′)-Val5-Hypertensin II-Asp1-β-amid

✍ Scribed by B. Riniker; R. Schwyzer

• Publisher: John Wiley and Sons
• Year: 1961
• Tongue: German
• Weight: 487 KB
• Volume: 44
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19610440311

✦ Synopsis

The syntheses of the chain‐homologues of hypertensin, H · Arg‐Val‐Tyr‐Val‐His‐Pro‐Phe · OH, H · Asp(NH~2~)‐Arg‐Val‐Tyr‐Val‐His‐Pro · OH, and H · Asp(R)‐Arg‐Val‐Tyr‐Tyr‐Val‐His‐Pro‐Phe · OH (R  −OH and −NH~2~), are described in detail. A system for the nomenclature of such analogues is proposed. The relative stability of H · Arg‐Val‐Tyr‐Val‐His‐Pro‐Phe · OH, H · Gly‐Arg‐Val‐Tyr‐Val‐His‐Pro‐Phe · OH~2~ and H · Asp(R)‐Arg‐Val‐Tyr‐Val‐His‐Pro‐Phe · OH in aqueous solution at 50° over a period of 6 months is discussed: the heptapeptide and Val^5^‐hypertensin II are very stable under these conditions, but the asparaginyl^1^‐ and glycyl^1^‐ compounds lose these residues to an extent of about 10%. A possible mechanism explaining the difference in the behaviour of the aspartyl and the asparaginyl residues is suggested.