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«Push-Pull»-Acetylene als Hilfsmittel zur Synthese von Peptiden

✍ Scribed by Markus Neuenschwander; Hans-Peter Fahrni; Ulrich Lienhard

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
999 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Peptide synthesis by Means of ‘Push‐Pull’‐Acetylenes

‘Push‐pull’‐acetylenes 1 are excellent reagents for peptide synthesis: Addition of ‘push‐pull’‐acetylenes to solutions of N‐protected amino acids (or vice versa) gives enol esters 5, which react selectively with the amino function of a second amino acid. In this way serine, tyrosine, 4‐hydroxyproline, cysteine as well as histidine are linked to form dipeptide esters without protection of the second functional group (OH, SH or NH). The amount of racemization is very low. Similarly tri‐ as well as tetrapeptides are available. The versatility of the reaction is discussed.

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**Attempted Synthesis of Push‐Pull Diacetylenes** Two alternative synthesis of push‐pull diacetylenes of type **1** (5‐amino‐2,4‐alkadiynals) are investigated. A bromination‐dehydrobromination sequence starting with 5‐dimethylamino‐2,4‐pentadienal (**2**) as well as the application of the well‐know