Chiral interaction in peptide molecules: effects of chiral peptide species on helix-sense induction in an N-terminal-free achiral peptide

Biopolymers
Yoshihito InaiYasuhiro Ookouchi

Abstract

Noncovalent chiral domino effect (NCDE) has been proposed as terminal-specific interaction upon a 3(10)-helical peptide chain, of which the helix sense is manipulated by an external chiral stimulus (mainly amino acid derivatives) operating on the N-terminus (Inai, Y., et al. J Am Chem Soc 2000, 122, 11731-11732; ibid., 2002, 124, 2466-2473; ibid., 2003, 125, 8151-8162). We have investigated here a helix-sense induction in an optically inactive N-terminal-free nonapeptide (1) through the screening of several peptide species that differ in chiral sequence, chain length, and C-terminal group. Helix-sense induction in peptide 1 depends largely on both the C-terminal chirality and carboxyl group in the external peptide, in which N-carbonyl-blocked amino acids, "monopeptide acids," should be the minimum requirement for effective induction. N-Protected mono- to tetrapeptides of L-Leu residue commonly induce a right-handed helix. NMR study and theoretical computation reveal that the N-terminal segment of peptide 1 binds the N-protected dipeptide molecule through multipoint coordination to induce a right-handed helix preferentially. The present findings not only will improve our understanding of the chiral roles in peptide or protein he...Continue Reading

References

Nov 12, 1975·Journal of the American Chemical Society·O PieroniF Ciardelli
Sep 1, 1991·Trends in Biochemical Sciences·C Toniolo, E Benedetti
Jun 5, 1988·Journal of Molecular Biology·D J Barlow, J M Thornton
Jan 1, 1996·Biopolymers·O PieroniV S Chauhan
Dec 10, 1997·Journal of Chromatography. B, Biomedical Sciences and Applications·D S Hage, S A Tweed
Aug 24, 2000·Accounts of Chemical Research·K B Lipkowitz
Feb 7, 2001·Proceedings of the National Academy of Sciences of the United States of America·U A RamagopalV S Chauhan
Mar 10, 2001·Nature·A SaghatelianM R Ghadiri
Nov 17, 2001·Chemical Reviews·J VenkatramanP Balaram
Nov 17, 2001·Chemical Reviews·R P ChengW F DeGrado
Mar 14, 2002·Journal of the American Chemical Society·Yoshihito InaiTadamichi Hirabayashi
Jun 13, 2002·Chemical Reviews·Hiroshi Tsukube, Satoshi Shinoda
Jan 14, 2003·Biomacromolecules·Yoshihito InaiTadamichi Hirabayashi
Dec 26, 2003·Chemistry : a European Journal·Eiji YashimaTatsuya Nishimura
Nov 4, 2004·Journal of the American Chemical Society·Vikas Nanda, William F Degrado
May 4, 1998·Angewandte Chemie·Yoshio Okamoto, Eiji Yashima
Dec 1, 2000·Angewandte Chemie·Igor A KozlovPeter E Nielsen

❮ Previous
Next ❯

Citations

Nov 8, 2011·Colloids and Surfaces. B, Biointerfaces·Feng ZhouHong Chen
Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
May 1, 2007·The Journal of Organic Chemistry·Hisatoshi Komori, Yoshihito Inai

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Yoshihito InaiNaoki Ousaka
Colloids and Surfaces. B, Biointerfaces
Feng ZhouHong Chen
Journal of the American Chemical Society
Taolei SunHarald Fuchs
Journal of the American Chemical Society
Kangjian TangHarald Fuchs
© 2021 Meta ULC. All rights reserved