» Articles » PMID: 22715982

Nucleation Effects in Peptide Foldamers

Overview
Journal J Am Chem Soc
Specialty Chemistry
Date 2012 Jun 22
PMID 22715982
Citations 18
Authors
Affiliations
Soon will be listed here.
Abstract

Oligomers composed of β(3)-amino acid residues and a mixture of α- and β(3)-residues have emerged as proteolytically stable structural mimics of α-helices. An attractive feature of these oligomers is that they adopt defined conformations in short sequences. In this manuscript, we evaluate the impact of β(3)-residues as compared to their α-amino acid analogs in prenucleated helices. Our hydrogen-deuterium exchange results suggest that heterogeneous sequences composed of "αααβ" repeats are conformationally more rigid than the corresponding homogeneous α-peptide helices, with the macrocycle templating the helical conformation having a significant influence.

Citing Articles

Design and Synthesis of Novel Helix Mimetics Based on the Covalent H-Bond Replacement and Amide Surrogate.

Liu J, Tang S, Yan J, Ye T Molecules. 2023; 28(2).

PMID: 36677838 PMC: 9863496. DOI: 10.3390/molecules28020780.


Identification of Secondary Binding Sites on Protein Surfaces for Rational Elaboration of Synthetic Protein Mimics.

Torner J, Yang Y, Rooklin D, Zhang Y, Arora P ACS Chem Biol. 2021; 16(7):1179-1183.

PMID: 34228913 PMC: 8344045. DOI: 10.1021/acschembio.1c00418.


Sulfono-γ-AApeptides as Helical Mimetics: Crystal Structures and Applications.

Sang P, Shi Y, Huang B, Xue S, Odom T, Cai J Acc Chem Res. 2020; 53(10):2425-2442.

PMID: 32940995 PMC: 8903043. DOI: 10.1021/acs.accounts.0c00482.


Macropinocytosis as a Key Determinant of Peptidomimetic Uptake in Cancer Cells.

Yoo D, Barros S, Brown G, Rabot C, Bar-Sagi D, Arora P J Am Chem Soc. 2020; 142(34):14461-14471.

PMID: 32786217 PMC: 7755425. DOI: 10.1021/jacs.0c02109.


Covalent Targeting of Ras G12C by Rationally Designed Peptidomimetics.

Yoo D, Hauser A, Joy S, Bar-Sagi D, Arora P ACS Chem Biol. 2020; 15(6):1604-1612.

PMID: 32378881 PMC: 7739374. DOI: 10.1021/acschembio.0c00204.


References
1.
Englander S, Kallenbach N . Hydrogen exchange and structural dynamics of proteins and nucleic acids. Q Rev Biophys. 1983; 16(4):521-655. DOI: 10.1017/s0033583500005217. View

2.
Driver R, Hoang H, Abbenante G, Fairlie D . A cyclic beta-strand tripeptide with an alpha-helix like CD spectrum. Org Lett. 2009; 11(14):3092-5. DOI: 10.1021/ol901181b. View

3.
Harker E, Daniels D, Guarracino D, Schepartz A . Beta-peptides with improved affinity for hDM2 and hDMX. Bioorg Med Chem. 2009; 17(5):2038-46. PMC: 2926950. DOI: 10.1016/j.bmc.2009.01.039. View

4.
Connelly G, Bai Y, Jeng M, Englander S . Isotope effects in peptide group hydrogen exchange. Proteins. 1993; 17(1):87-92. DOI: 10.1002/prot.340170111. View

5.
Price J, Seth Horne W, Gellman S . Structural consequences of beta-amino acid preorganization in a self-assembling alpha/beta-peptide: fundamental studies of foldameric helix bundles. J Am Chem Soc. 2010; 132(35):12378-87. PMC: 2981134. DOI: 10.1021/ja103543s. View