NDLI: Design, conformational studies and analysis of structure–function relationships of PTH (1–11) analogues: the essential role of Val in position 2

Content Provider	Springer Nature Link
Author	Caporale, A. Gesiot, L. Sturlese, M. Wittelsberger, A. Mammi, S. Peggion, E.
Copyright Year	2011
Abstract	The N-terminal 1–34 segment of parathyroid hormone (PTH) is fully active in vitro and in vivo and it elicits all the biological responses characteristic of the native intact PTH. Recent studies reported potent helical analogues of the PTH (1–11) with helicity-enhancing substitutions. This work describes the synthesis, biological activity, and conformational studies of analogues obtained from the most active non-natural PTH (1–11) peptide H-Aib-Val-Aib-Glu-Ile-Gln-Leu-Nle-His-Gln-Har-NH2; specifically, the replacement of Val in position 2 with d-Val, l-(αMe)-Val and N-isopropyl-Gly was studied. The synthesized analogues were characterized functionally by in-cell assays and their structures were determined by CD and NMR spectroscopy. To clarify the relationship between the structure and activity, the structural data were used to generate a pharmacophoric model, obtained overlapping all the analogues. This model underlines the fundamental functional role of the side chain of Val2 and, at the same time, reveals that the introduction of conformationally constrained Cα-tetrasubstituted α-amino acids in the peptides increases their helical content, but does not necessarily ensure significant biological activity.
Starting Page	207
Ending Page	218
Page Count	12
File Format	PDF
ISSN	09394451
Journal	Amino Acids
Volume Number	43
Issue Number	1
e-ISSN	14382199
Language	English
Publisher	Springer Vienna
Publisher Date	2011-09-15
Publisher Place	Vienna
Access Restriction	Subscribed
Subject Keyword	PTH NMR analysis Pharmacophoric model αMeVal Conformational analogues Structure/activity analysis Life Sciences Proteomics Biochemical Engineering Biochemistry Neurobiology Analytical Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Clinical Biochemistry

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