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Synthesis of Poly‐Aib Oligopeptides and Aib‐Containing Peptides via the ‘Azirine/Oxazolone Method’, and Their Crystal Structures
Author(s) -
DanneckerDörig Ingeborg,
Linden Anthony,
Heimgartner Heinz
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100116
Subject(s) - chemistry , oxazolone , azirine , oligopeptide , synthon , peptide , amine gas treating , stereochemistry , crystal structure , amino acid , crystallography , organic chemistry , biochemistry , ring (chemistry)
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‐2 H ‐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)/ZnCl 2 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 3 10 ‐helical conformation of Aib peptides.