Publication Date:
2011-06-15
Description:
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.
Print ISSN:
0018-019X
Electronic ISSN:
1522-2675
Topics:
Chemistry and Pharmacology
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