Chemical modifications designed to improve peptide stability: incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclization

L Gentilucci, R De Marco… - Current pharmaceutical …, 2010 - ingentaconnect.com
Functions and properties of native peptides vary from highly specific antibiotics or cytotoxic
antitumor drugs, to hormones, neurotransmitters, immunomodulators, etc. Despite their …

Overcoming the shortcomings of peptide-based therapeutics

C Lamers - Future Drug Discovery, 2022 - Taylor & Francis
Peptides have traditionally been perceived as poor drug candidates due to unfavorable
characteristics mainly regarding their pharmacokinetic behavior, including plasma stability …

Flexizymes for genetic code reprogramming

Y Goto, T Katoh, H Suga - Nature protocols, 2011 - nature.com
Genetic code reprogramming is a method for the reassignment of arbitrary codons from
proteinogenic amino acids to nonproteinogenic ones; thus, specific sequences of …

Natural product-like macrocyclic N-methyl-peptide inhibitors against a ubiquitin ligase uncovered from a ribosome-expressed de novo library

Y Yamagishi, I Shoji, S Miyagawa, T Kawakami… - Chemistry & biology, 2011 - cell.com
Naturally occurring peptides often possess macrocyclic and N-methylated backbone. These
features grant them structural rigidity, high affinity to targets, proteolytic resistance, and …

Late-Stage β-C(sp3)–H Deuteration of Carboxylic Acids

A Uttry, S Mal, M van Gemmeren - Journal of the American …, 2021 - ACS Publications
Carboxylic acids are highly abundant in bioactive molecules. In this study, we describe the
late-stage β-C (sp3)–H deuteration of free carboxylic acids. On the basis of the finding that C …

Formation of α-chiral centers by asymmetric β-C(sp3)–H arylation, alkenylation, and alkynylation

QF Wu, PX Shen, J He, XB Wang, F Zhang, Q Shao… - Science, 2017 - science.org
The enzymatic β-C–H hydroxylation of the feedstock chemical isobutyric acid has enabled
the asymmetric synthesis of a wide variety of polyketides. The analogous transition metal …

Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids

C Cativiela, MD Díaz-de-Villegas - Tetrahedron: Asymmetry, 2007 - Elsevier
Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids -
ScienceDirect Skip to main contentSkip to article Elsevier logo Journals & Books Search …

Design of a mimic of nonamyloidogenic and bioactive human islet amyloid polypeptide (IAPP) as nanomolar affinity inhibitor of IAPP cytotoxic fibrillogenesis

LM Yan, M Tatarek-Nossol, A Velkova… - Proceedings of the …, 2006 - National Acad Sciences
Protein aggregation into cytotoxic oligomers and fibrils in vivo is linked to cell degeneration
and the pathogenesis of> 25 uncurable diseases, whereas the high aggregation propensity …

Strategies to improve the physicochemical properties of peptide-based drugs

MF Lee, CL Poh - Pharmaceutical Research, 2023 - Springer
Peptides are a rapid-growing class of therapeutics with unique and desirable
physicochemical properties. Due to disadvantages such as low membrane permeability and …

Messenger RNA-programmed incorporation of multiple N-methyl-amino acids into linear and cyclic peptides

T Kawakami, H Murakami, H Suga - Chemistry & Biology, 2008 - cell.com
Natural peptide products often contain N-methylated backbones, and such a modification
plays a crucial role in making natural peptides peptidase resistant and membrane …