Synthese einer geschützten Pentapeptid-Sequenz des Tyrocidins A unter Verwendung farbiger Schutzgruppen und des p-Nitrobenzyl-Restes
✍ Scribed by R. Schwyzer; P. Sieber
- Book ID
- 102248874
- Publisher
- John Wiley and Sons
- Year
- 1959
- Tongue
- German
- Weight
- 365 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Using p‐(p′‐methoxy‐phenylazo)‐benzyloxycarbonyl‐(MZ‐) and p‐nitrobenzyl‐(NB‐) as blocking groups for the ct‐amino‐ and a‐carboxylic functions respectively, a completely protected pentapeptide unit, occurring in tyrocidine A, has been prepared: MZ‐L‐Phe‐D‐Phe‐L‐Asp(OCH,)‐L‐Glu(OCH,)‐L‐Tyr(OAc) ONB. The p‐nitrobenzyl‐ester group is very resistant towards HBr in acetic acid, the reagent used for intermediary splitting of the MZ‐groups. Peptide bonds were formed by means of either POCl~3~, + triethylamine or by dicyclohexyl‐carbodiimide. All the products containing MZ‐groups were obtained in the crystalline state.