NDLI: Structural Dimorphism of Achiral α,γ-Hybrid Peptide Foldamers: Coexistence of 12- and 15/17-Helices

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Structural Dimorphism of Achiral α,γ-Hybrid Peptide Foldamers: Coexistence of 12- and 15/17-Helices

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Hofmann, Hans-jörg George, Gijo Raja, K. Muruga Poopathi Saseendran, Abhijith Raghothama, Srinivasarao Gopi, Hosahudya N. Misra, Rajkumar Veeresh, Kuruva
Description	Author Affiliation: Misra R ( Department of Chemistry, Indian Institution of Science Education and Research, Dr. Homi Bhabha Road, Pune, 411021, India.); Saseendran A ( Department of Chemistry, Indian Institution of Science Education and Research, Dr. Homi Bhabha Road, Pune, 411021, India.); George G ( NMR Research Center, Indian Institute of Science, Bangalore, 560012, India.); Veeresh K ( Department of Chemistry, Indian Institution of Science Education and Research, Dr. Homi Bhabha Road, Pune, 411021, India.); Raja KM ( Department of Physical Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, 625 021, India.); Raghothama S ( NMR Research Center, Indian Institute of Science, Bangalore, 560012, India.); Hofmann HJ ( Institute of Biochemistry, Faculty of Biosciences, Pharmacy and Psychology, Talstraße 33, 04103, Leipzig, Germany.); Gopi HN ( Department of Chemistry, Indian Institution of Science Education and Research, Dr. Homi Bhabha Road, Pune, 411021, India.)
Abstract	Here, novel 12-helices in α,γ-hybrid peptides composed of achiral α-aminoisobutyric acid (Aib) and 4-aminoisocaproic acid (Aic, doubly homologated Aib) monomers in 1:1 alternation are reported. The 12-helices were indicated by solution and crystal structural analyses of tetra- and heptapeptides. Surprisingly, single crystals of the longer nonapeptide displayed two different helix types: the novel 12-helix and an unprecedented 15/17-helix. Quantum chemical calculations on both helix types in a series of continuously lengthened Aib/Aic-hybrid peptides confirm that the 12-helix is more stable than the 15/17-helix in shorter peptides, whereas the 15/17-helix is more stable in longer sequences. Thus, the coexistence of both helix types can be expected within a definite range of sequence lengths. The novel 15/17- and 12-helices in α,γ-hybrid peptides with 5→1 and 4→1 hydrogen-bonding patterns, respectively, can be viewed as backbone-expanded analogues of native α- and $3_{10}-helices.$
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	15
Volume Number	23
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2017-03-13
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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