Stabilizing Bifurcated Hydrogen Bond in 8-Aminoquinoline Appended Peptides.

Autor: Shekhar S; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, 226031, Lucknow, India.; Academy of Scientific and Innovative Research (AcSIR), 201002, Ghaziabad, India., Meena R; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, 226031, Lucknow, India.; Academy of Scientific and Innovative Research (AcSIR), 201002, Ghaziabad, India., Lal J; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, 226031, Lucknow, India.; Academy of Scientific and Innovative Research (AcSIR), 201002, Ghaziabad, India., Yadav M; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, 226031, Lucknow, India., Kant R; Division of Biochemistry and Structural Biology, CSIR-Central Drug Research Institute, 226031, Lucknow, India., Reddy DN; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, 226031, Lucknow, India.; Academy of Scientific and Innovative Research (AcSIR), 201002, Ghaziabad, India.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2024 Jul 15; Vol. 19 (14), pp. e202400248. Date of Electronic Publication: 2024 Jun 11.
DOI: 10.1002/asia.202400248
Abstrakt: The hydrogen bonding interaction between an amide N-H and the amide N of the preceding residue is prevalent in proline-containing proteins and peptides. However, the N-H⋅⋅⋅N hydrogen bonding interaction is rare in non-prolyl natural peptides due to restricted dihedral angles. Herein, we stabilize this type of interaction in 8-aminoquinoline appended non-prolyl peptides through bifurcated N⋅⋅⋅H⋅⋅⋅N hydrogen bond. The 8-aminoquinoline-incorporated model peptides 2 a-i were designed, synthesized, and the crystal structures of 2 a-c and 2 i were solved. Analysis of crystal data reveals that the amide N-H of aminoquinoline is involved in bifurcated hydrogen bonding interaction with the nitrogen of the preceding amino acid residue and the nitrogen in quinoline. Analysis of crystal packing, Hirshfeld surface and fingerprint plots confirms that the intermolecular O⋅⋅⋅H contacts significantly contribute to stabilizing bifurcated N⋅⋅⋅H⋅⋅⋅N hydrogen bonding interaction. Furthermore, NMR experiments and CD spectroscopy were conducted to examine the preferred conformation in solution, and the data corroborate with the crystal structure conformation.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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