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Synthesis of a new azapeptide with renin-inhibiting properties

✍ Scribed by Gante, Joachim ;Weitzel, Reinhard

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
207 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Boc‐hydrazine (1) was treated with 4‐nitrophenyl chloroformate (2) to give Boc‐Azagly 4‐nitrophenyl ester (3). Reaction of 3 with H‐ACHP‐Ile‐3‐pyridylmethylamide^5)^ (4) provided Boc‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide (5). This was deprotected with HCl/dioxane to give H‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide dihydrochloride (6), which was coupled with Boc‐Phe‐OH (7) by the carbodiimide/HOBt method providing the final azapeptide Boc‐Phe‐Azagly‐ACHP‐3‐pyridyl‐methylamide (8). This compound was shown to be a renin inhibitor of high specificity.

📜 SIMILAR VOLUMES

Synthesis of a Renin Inhibitor of the Az
Synthesis of a Renin Inhibitor of the Azapeptide Type
✍ Gante, Joachim ;Kahlenberg, Harald 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 English ⚖ 294 KB

In 1962 "azapeptides" were described for the first time'). In these peptide analogs the a-CH group of one or more amino acid residues of a peptide chain is replaced with nitrogen.

Synthesis and Biological Activity of a P
Synthesis and Biological Activity of a Potent Renin Inhibitor of the Azapeptide Type
✍ Gante, Joachim ;Krug, Michael ;Lauterbach, Günter ;Weitzel, Reinhard 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 286 KB

## Abstract A highly potent renin inhibitor of the azapeptide type (2) is synthesized by starting from the hydrazine derivative 3. This peptide analogue inhibits renin in the same range (nanomolar) as its purely peptidic original 2a, but reveals much higher specificity for renin than 2a does.