A Peptoid
with Extended Shape in Water
Posted on 2019-08-23 - 19:14
The
term “peptoids” was introduced decades ago to
describe peptide analogues that exhibit better physicochemical and
pharmacokinetic properties than peptides. Oligo(N-substituted glycine) (oligo-NSG) was previously proposed as a peptoid
due to its high proteolytic resistance and membrane permeability.
However, oligo-NSG is conformationally flexible, and ensuring a defined
shape in water is difficult. This conformational flexibility severely
limits the biological application of oligo-NSG. Here, we propose oligo(N-substituted alanine) (oligo-NSA) as a peptoid that forms
a defined shape in water. The synthetic method established in this
study enabled the first isolation and conformational study of optically
pure oligo-NSA. Computational simulations, crystallographic studies,
and spectroscopic analysis demonstrated the well-defined extended
shape of oligo-NSA realized by backbone steric effects. This new class
of peptoid achieves the constrained conformation without any assistance
of N-substituents and serves as a scaffold for displaying
functional groups in well-defined three-dimensional space in water,
which leads to effective biomolecular recognition.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Morimoto, Jumpei; Fukuda, Yasuhiro; Kuroda, Daisuke; Watanabe, Takumu; Yoshida, Fumihiko; Asada, Mizue; et al. (2019). A Peptoid
with Extended Shape in Water. ACS Publications. Collection. https://doi.org/10.1021/jacs.9b04371
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (11)
JM
Jumpei Morimoto
YF
Yasuhiro Fukuda
DK
Daisuke Kuroda
TW
Takumu Watanabe
FY
Fumihiko Yoshida
MA
Mizue Asada
TN
Toshikazu Nakamura
AS
Akinobu Senoo
SN
Satoru Nagatoishi
KT
Kouhei Tsumoto
SS
Shinsuke Sando