Proline Analogues in Drug Design: Current Trends and Future Prospects

V Kubyshkin, PK Mykhailiuk - Journal of Medicinal Chemistry, 2024 - ACS Publications
Proline analogues are versatile chemical building blocks that enable modular construction
of small-molecule drugs and pharmaceutical peptides. Over the past 15 years, the FDA has …

Solution structure of kistrin, a potent platelet aggregation inhibitor and GP IIb-IIIa antagonist

M Adler, RA Lazarus, MS Dennis, G Wagner - Science, 1991 - science.org
The structure of kistrin, which is a member of a homologous family of glycoprotein IIb-IIIa (GP
IIb-IIIa) antagonists and potent protein inhibitors of platelet aggregation, has been …

Steric Effects on the Amide Isomer Equilibrium of Prolyl Peptides. Synthesis and Conformational Analysis of N-Acetyl-5-tert-butylproline N'-Methylamides

E Beausoleil, WD Lubell - Journal of the American Chemical …, 1996 - ACS Publications
The influence of a bulky 5-position substituent on the amide isomer equilibrium N-terminal to
proline has been explored via the synthesis and analysis of N-(acetyl) proline N ' …

Photochemical in-flow synthesis of 2, 4-methanopyrrolidines: pyrrolidine analogues with improved water solubility and reduced lipophilicity

VV Levterov, O Michurin, PO Borysko… - The Journal of …, 2018 - ACS Publications
A practical synthesis of 2, 4-methanopyrrolidines was elaborated. The key synthetic step
was an intramolecular photochemical [2+ 2]-cycloaddition of an acrylic acid derivative in …

Retention of the cis proline conformation in tripeptide fragments of bovine pancreatic ribonuclease A containing a non-natural proline analogue, 5, 5-dimethylproline

SSA An, CC Lester, JL Peng, YJ Li… - Journal of the …, 1999 - ACS Publications
Attention is focused on l-5, 5-dimethylproline (dmP) as a substitute to lock l-proline (Pro) in a
cis conformation in peptides and proteins, to prevent cis/trans isomerization when a protein …

Topographic design of peptide neurotransmitters and hormones on stable backbone templates: relation of conformation and dynamics to bioactivity

WM Kazmierski, HI Yamamura… - Journal of the American …, 1991 - ACS Publications
We have proposed that development of methods for controlling theside-chain topography of
amino acid residues in peptides and proteins provides a new approach to the topographical …

Substituted 2-azabicyclo [2.1. 1] hexanes as constrained proline analogues: implications for collagen stability

CL Jenkins, G Lin, J Duo, D Rapolu… - The Journal of …, 2004 - ACS Publications
Among the proteinogenic amino acids, only proline is a secondary amine and only proline
has a saturated ring. Electronegative substituents on C-4 (that is, Cγ) have a substantial …

4-Fluoro-2, 4-methanoproline

AN Tkachenko, DS Radchenko, PK Mykhailiuk… - Organic …, 2009 - ACS Publications
The first fluorinated analogue of the naturally occurring 2, 4-methanoproline, 4-fluoro-2, 4-
methanoproline, has been synthesized in five steps from commercially available methyl 2 …

Bovine pancreatic ribonuclease A: oxidative and conformational folding studies

HA Scheraga, WJ Wedemeyer, E Welker - Methods in enzymology, 2001 - Elsevier
For many years, bovine pancreatic ribonuclease A (RNase A, EC 3.1. 27.5) has been a
model protein for studies of protein structure, energetics, disulfide-bond reactions, and …

Total synthesis of cyclobutane amino acids from Atelia herbert smithii

P Hughes, J Clardy - The Journal of Organic Chemistry, 1988 - ACS Publications
Total synthesis of cyclobutane amino acids from Atelia herbert smithii Page 1 J. Org. Chem.
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