Proline Analogues

V Kubyshkin, M Rubini - Chemical Reviews, 2024 - ACS Publications
Within the canonical repertoire of the amino acid involved in protein biogenesis, proline
plays a unique role as an amino acid presenting a modified backbone rather than a side …

Biocatalysis with unnatural amino acids: enzymology meets xenobiology

F Agostini, JS Völler, B Koksch… - Angewandte Chemie …, 2017 - Wiley Online Library
The goal of xenobiology is to design biological systems endowed with unusual biochemical
functions, whereas enzymology concerns the study of enzymes, the workhorses of …

Predicting collagen triple helix stability through additive effects of terminal residues and caps

T Fiala, EP Barros, R Heeb, S Riniker… - Angewandte Chemie …, 2023 - Wiley Online Library
Collagen model peptides (CMPs) consisting of proline‐(2S, 4R)‐hydroxyproline‐glycine
(POG) repeats have provided a breadth of knowledge of the triple helical structure of …

Prospects of In vivo Incorporation of Non-canonical Amino Acids for the Chemical Diversification of Antimicrobial Peptides

T Baumann, JH Nickling, M Bartholomae… - Frontiers in …, 2017 - frontiersin.org
The incorporation of non-canonical amino acids (ncAA) is an elegant way for the chemical
diversification of recombinantly produced antimicrobial peptides (AMPs). Residue-and site …

Fluorine-containing prolines: Synthetic strategies, applications, and opportunities

PK Mykhailiuk - The Journal of Organic Chemistry, 2022 - ACS Publications
Fluorinated prolines play an important role in peptide studies, protein engineering,
medicinal chemistry, drug discovery, and agrochemistry. Since the first synthesis of 4 …

Stabilization of the triple helix in collagen mimicking peptides

V Kubyshkin - Organic & Biomolecular Chemistry, 2019 - pubs.rsc.org
Collagen mimics are peptides designed to reproduce structural features of natural collagen.
A triple helix is the first element in the hierarchy of collagen folding. It is an assembly of three …

Biochemistry of fluoroprolines: The prospect of making fluorine a bioelement

V Kubyshkin, R Davis, N Budisa - Beilstein journal of organic …, 2021 - beilstein-journals.org
Due to the heterocyclic structure and distinct conformational profile, proline is unique in the
repertoire of the 20 amino acids coded into proteins. Here, we summarize the biochemical …

Peptidyl-prolyl model study: how does the electronic effect influence the amide bond conformation?

PK Mykhailiuk, V Kubyshkin, T Bach… - The Journal of organic …, 2017 - ACS Publications
The triple-helical structure of collagen, the most abundant protein in animal bodies, owes its
stability to post-translationally installed hydroxyl groups at position 4 of prolyl residues. To …

4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study

IG Logvinenko, IV Sadkova, NA Tolmachova… - Organic & …, 2024 - pubs.rsc.org
All four stereoisomers of 4-CF3O-proline have been synthesized through a
fluorodesulfurization approach using the corresponding 4-hydroxyprolines as starting …

Biokatalyse mit nicht‐natürlichen Aminosäuren: Enzymologie trifft Xenobiologie

F Agostini, JS Völler, B Koksch… - Angewandte …, 2017 - Wiley Online Library
Abstract Das Ziel der Xenobiologie ist das Design von biologischen Systemen, die mit nicht‐
natürlichen biochemischen Funktionen ausgestattet sind, während die Enzymologie sich mit …