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Conformational properties of 2,3-methanopyroglutamic acid in peptides: Nmr and X-ray diffraction studies

✍ Scribed by C. Mapelli; L. F. Elrod; F. L. Switzer; C. H. Stammer; E. M. Holt

Publisher: Wiley (John Wiley & Sons)
Year: 1989
Tongue: English
Weight: 269 KB
Volume: 28
Category: Article
ISSN: 0006-3525
DOI: 10.1002/bip.360280114

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✦ Synopsis

The effects of replacing L-pyroglutamic acid with the cyclopropane analogue 2,3-methanopyroglutamic acid (2,3-MeGlp) on conformation and enzymatic stability have been investigated in 2,3-MeGlp-NHMe and the novel thyrotropin releasing hormone (TRH) analogue [2,3-MeGlp1]-TRH by x-ray diffraction and nmr. While 2,B-MeGlp-NHMe adopts a folded conformation (small 4 angle) in the solid state, several conformations are available to the molecule in solution. 'H-nmr of the diastereomeric mixture [( &)-2,3-MeGlp1]-TRH indicates a close orientation of the pyrrolidone and imidazole Mgs. The 2,B-MeGlp-His amide bond is considerably more stable to pyroglutamate aminopeptidase than the Glp-His bond in TRH.

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