NDLI: Stabilization of peptides against proteolysis through disulfide-bridged conjugation with synthetic aromatics

Content Provider	Royal Society of Chemistry (RSC)
Author	Li, Tao Wang, Jinghui Li, Jianguo Wu, Chuanliu Chen, Yaqi Verma, Chandra Zhao, Yibing Cheng, Shiyan
Copyright Year	2017
Abstract	Peptides have been promising molecular scaffolds for the development of potential therapeutics with high affinity and specificity to biomacromolecules. However, their inherent proteolytic instability significantly hampers their biological applications. Strategies that can stabilize peptides against proteolytic digestion on the basis of noncovalent interactions—without extensive manipulation of the sequence or use of unnatural residues—are greatly desired. In this work, we developed a general, convenient, and efficient strategy for the stabilization of peptides against proteolysis, which involves noncovalent π–π interactions between aromatic amino acid residues in peptides and synthetic electron-deficient aromatics (NDI), together with the implication of steric hindrance (from the bulky NDI moiety), and the enhancement of peptide α-helicity. This strategy is complementary in concept to the conventional well-established covalent approaches for peptide stabilization, and is thus promising for being utilized, in combination with the latter ones, to circumvent the problem of proteolytic instability of peptides. We envisioned that this study should provide invaluable guidelines to the design and synthesis of organic molecule–peptide hybrids with significantly improved proteolytic resistance, and benefit the development of peptide therapeutics and probes.
Starting Page	1921
Ending Page	1929
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	15
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c6ob02786e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	NDI Protease Carboxylic acid Covalent bond Biomacromolecules Steric effects Peptide
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis

Dynamic covalent chemistry in aqueous solution by photoinduced radical disulfide metathesis

Steric effects in the hydrolysis of formaldehyde methyl aryl acetals

Dopamine selective molecularly imprinted polymers via post-imprinting modification

Creating carbon–carbon bonds with samarium diiodide for the synthesis of modified amino acids and peptides

The sergeants-and-soldiers effect: chiral amplification in naphthalenediimide nanotubes

Bromohydrin formation in aqueous dimethyl sulphoxide; electronic and steric effects

Aggregation modes in sheets formed by protected β-amino acids and β-peptides

Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

Stabilization of peptides against proteolysis through disulfide-bridged conjugation with synthetic aromatics

Similar Documents

Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis

Dynamic covalent chemistry in aqueous solution by photoinduced radical disulfide metathesis

Steric effects in the hydrolysis of formaldehyde methyl aryl acetals

Dopamine selective molecularly imprinted polymers via post-imprinting modification

Creating carbon–carbon bonds with samarium diiodide for the synthesis of modified amino acids and peptides

The sergeants-and-soldiers effect: chiral amplification in naphthalenediimide nanotubes

Bromohydrin formation in aqueous dimethyl sulphoxide; electronic and steric effects

Aggregation modes in sheets formed by protected β-amino acids and β-peptides

Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

Stabilization of peptides against proteolysis through disulfide-bridged conjugation with synthetic aromatics