Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

N Seo, H Son, Y Kim, IA Guzei, P Kang, SH Choi - Organic Letters, 2023 - ACS Publications
We explored trans-and cis-2-aminocycloheptanecarboxylic acid (ACHpC) as potential
building blocks for helical foldamers. trans-ACHpC does not show sufficient folding …

Fluoro-Aryl Substituted α,β2,3-Peptides in the Development of Foldameric Antiparallel β-Sheets: A Conformational Study

R Bucci, A Contini, F Clerici, EM Beccalli… - Frontiers in …, 2019 - frontiersin.org
α, β2, 3-Disteroisomeric foldamers of general formula Boc (S-Ala-β-2 R, 3 R-Fpg) nOMe or
Boc (S-Ala-β-2 S, 3 S-Fpg) nOMe were prepared from both enantiomers of syn H-2-(2-F …

Stabilization of 11/9-helical α/β-peptide foldamers in protic solvents

M Lee, J Shim, P Kang, MG Choi… - Chemical Communications, 2016 - pubs.rsc.org
α/β-Peptides with alternating α-amino acid and cis-2-aminocyclohexanecarboxylic acid (cis-
ACHC) residues adopt 11/9-helical conformations, the folding propensity of which …

Design and synthesis of peptides with hybrid helix-turn-helix (HTH) motif and their conformational study

GVM Sharma, P Thodupunuri, K Sirisha… - The Journal of …, 2014 - ACS Publications
The present study is aimed at the design and synthesis of peptides with hybrid helix-turn-
helix (HTH) motif and their conformational analysis (NMR, MD, and CD studies). The …

Design and synthesis of novel oxetane β3-amino acids and α, β-peptides

GVM Sharma, G Venkateshwarlu, S Katukuri… - Tetrahedron, 2015 - Elsevier
The study describes synthesis of (S)-and (R)-oxetane-β 3-amino acid (β 3-Oaa) monomers
from diacetone glucose (DAG). The oxetane ring is prepared by a nucleophilic cyclization …

C11/C9 Helical Folding in αβ Hybrid Peptides Containing 1‐Amino‐cyclohexane acetic acid (β3, 3‐Ac6c)

NA Wani, S Raghothama, UP Singh… - Chemistry–A European …, 2017 - Wiley Online Library
The present study describes the solid‐state conformation of αβ hybrid peptides, Boc‐Leu‐
β3, 3‐Ac6c‐OH, P1; Boc‐Leu‐β3, 3‐Ac6c‐Leu‐β3, 3‐Ac6c‐OMe, P2; and Boc‐Leu‐β3, 3 …

Side chain-specific 11/9-helix propensity of α/β-peptides with alternating residue types

J Lee, J Shim, P Kang, MG Choi… - Organic & Biomolecular …, 2018 - pubs.rsc.org
The 11/9-helix is among the most stable and non-traditional helical structures for α/β-
peptides with alternating residue types. The effect of side chain groups of α-residues and β3 …

cis-2-Aminocyclohex-4-enecarboxylic acid as a new building block of helical foldamers

S Kwon, P Kang, MG Choi, SH Choi - New Journal of Chemistry, 2015 - pubs.rsc.org
cis-2-Aminocyclohex-4-enecarboxylic acid (cis-ACHE) is a conformationally constrained β-
amino acid. We showed that the conformational preference of a cis-ACHE residue is similar …

Synthesis and conformational studies of α/β 2, 3-peptides derived from alternating β 2, 3-amino acids and l-Ala repeats

GVM Sharma, T Sridhar, B Veena, PP Reddy… - New Journal of …, 2015 - pubs.rsc.org
Cyclic β2, 3-amino acids though have been extensively used in foldamer designs, their
acyclic analogues have received less attention. In view of strong backbone constraints …

Asymmetric synthesis of aminocyclooctenecarbonitriles: Cyclooctene β-lactam and hydroxyaminocyclooctene carboxylic precursors

BO Aydin, E Yurtoglu, N Arcelik, E Sahin, H Secen… - Tetrahedron …, 2019 - Elsevier
Enantiopure β-aminocyclooctenenitriles, as precursors of β-amino acids and β-lactams,
were synthesized from a readily available chloroalkene nitrile and (S)-methylbenzylamine …