Synthesis of Poly‐Aib Oligopeptides and Aib‐Containing Peptides via the ‘Azirine/Oxazolone Method’, and Their Crystal Structures |
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Authors: | Anthony Linden Heinz Heimgartner |
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Affiliation: | 1. Organisch‐Chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41?44?635?4282;2. fax: +41?44?635?6812) |
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Abstract: | The protected poly‐Aib oligopeptides Z‐(Aib)n‐N(Me)Ph with n=2–6 were prepared according to the ‘azirine/oxazolone method’, i.e., by coupling amino or peptide acids with 2,2,N‐trimethyl‐N‐phenyl‐2H‐azirin‐3‐amine ( 1a ) as an Aib synthon (Scheme 2). Following the same concept, the segments Z‐(Aib)3‐OH ( 9 ) and H‐L ‐Pro‐(Aib)3‐N(Me)Ph ( 20 ) were synthesized, and their subsequent coupling with N,N′‐dicyclohexylcarbodiimide (DCC)/ZnCl2 led to the protected heptapeptide Z‐(Aib)3‐L ‐Pro‐(Aib)3‐N(Me)Ph ( 21 ; Scheme 3). The crystal structures of the poly‐Aib oligopeptide amides were established by X‐ray crystallography confirming the 310‐helical conformation of Aib peptides. |
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Keywords: | Oligopeptides 2‐Aminoisobutyric acid (Aib) Peptides Azirine/oxazolone method X‐Ray crystallography |
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