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Digitale Medien

Conformational properties of 2,3-methanopyroglutamic acid in peptides: Nmr and X-ray diffraction studies (1989)

Mapelli, C. ; Elrod, L. F. ; Switzer, F. L. ; [weitere]

New York : Wiley-Blackwell

Biopolymers 28 (1989), S. 123-128

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Details

ISSN: 0006-3525

Schlagwort(e): Chemistry ; Polymer and Materials Science

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 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 2,3-MeGlp-NHMe adopts a folded conformation (small ψ angle) in the solid state, several conformations are available to the molecule in solution. 1H-nmr of the diastereomeric mixture [(±)-2,3-MeGlp1]-TRH indicates a close orientation of the pyrrolidone and imidazole rings. The 2,3-MeGlp-His amide bond is considerably more stable to pyroglutamate aminopeptidase than the Glp-His bond in TRH.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/bip.360280114

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