DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Spiroligomer‐Based Macrocycles for Atomically Precise Membranes

Journal Article · · Angewandte Chemie (International Edition)

Abstract Here, we report a new class of peptidomimetic macrocycles with well‐defined three‐dimensional structures and low conformational flexibility. They are assembled from fused‐ring spiro‐ladder oligomers (spiroligomers) by modular solid‐phase synthesis. Two‐dimensional nuclear magnetic resonance confirms their shape persistency. Triangular macrocycles of tunable sizes assemble into membranes with atomically precise pores, which exhibit size and shape‐dependent molecular sieving towards a series of structurally similar compounds. The exceptional structural diversity and stability of spiroligomer‐based macrocycles will be explored for more applications.

Research Organization:
Mainstream Engineering Corporation, Rockledge, FL (United States)
Sponsoring Organization:
USDOE; USDOE Office of Science (SC)
Grant/Contract Number:
SC0017037
OSTI ID:
1975167
Journal Information:
Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 27 Vol. 62; ISSN 1433-7851
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (43)

Cyclodextrin Films with Fast Solvent Transport and Shape-Selective Permeability journal April 2017
Precise Molecular Sieving Architectures with Janus Pathways for Both Polar and Nonpolar Molecules journal January 2018
Struktur und Biogenese der Makrolide journal January 1957
Cavitands as Containers for α,ω‐Dienes and Chaperones for Olefin Metathesis journal November 2018
Synthesis and Screening of a DNA‐Encoded Library of Non‐Peptidic Macrocycles** journal March 2022
Manganese‐Catalyzed Asymmetric Formal Hydroamination of Allylic Alcohols: A Remarkable Macrocyclic Ligand Effect journal May 2022
Recent Advances in the Synthesis of Peptoid Macrocycles journal February 2018
Artificial Water Channels: Towards Biomimetic Membranes for Desalination journal November 2020
Lorlatinib in patients with ALK-positive non-small-cell lung cancer: results from a global phase 2 study journal December 2018
DNA-encoded chemical libraries of macrocycles journal June 2015
An improved method for the solution cyclization of peptides under pseudo-high dilution conditions journal August 2004
Design, synthesis, and diversification of ribosomally derived peptide macrocycles journal August 2013
Molecular Recognition in Water Using Macrocyclic Synthetic Receptors journal January 2021
Rationalization of the Membrane Permeability Differences in a Series of Analogue Cyclic Decapeptides journal November 2018
Block Copolymer Membranes for Aqueous Solution Applications journal March 2016
Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers journal May 2022
Gas Transport across Hyperthin Membranes journal January 2013
2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products journal April 2012
Review: A History of Cyclodextrins journal September 2014
Cross relaxation without TOCSY: transverse rotating-frame Overhauser effect spectroscopy journal April 1992
The Synthesis of Functionalized Nanoscale Molecular Rods of Defined Length journal March 2003
Cyclic Peptoids journal March 2007
Extreme Stabilization and Redox Switching of Organic Anions and Radical Anions by Large-Cavity, CH Hydrogen-Bonding Cyanostar Macrocycles journal November 2016
Subnanometer Porous Thin Films by the Co-assembly of Nanotube Subunits and Block Copolymers journal January 2011
Light-powered autonomous and directional molecular motion of a dissipative self-assembling system journal November 2014
An artificial molecular pump journal May 2015
Molecularly-porous ultrathin membranes for highly selective organic solvent nanofiltration journal November 2020
Second-generation DNA-templated macrocycle libraries for the discovery of bioactive small molecules journal April 2018
Aligned macrocycle pores in ultrathin films for accurate molecular sieving journal August 2022
Design, synthesis and applications of responsive macrocycles journal December 2020
Macrocycles: lessons from the distant past, recent developments, and future directions journal January 2015
Progress towards the broad use of non-peptide synthetic macrocycles in drug discovery journal January 2017
Conformational isomerism in cyclic peptoids and its specification journal January 2017
Pillararenes as macrocyclic hosts: a rising star in metal ion separation journal January 2019
Cyclic peptides: backbone rigidification and capability of mimicking motifs at protein–protein interfaces journal January 2021
Stable pseudo[3]rotaxanes with strong positive binding cooperativity based on shape-persistent aromatic oligoamide macrocycles journal January 2021
The coming of age of water channels for separation membranes: from biological to biomimetic to synthetic journal January 2022
Structure prediction of cyclic peptides by molecular dynamics + machine learning journal January 2021
Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry journal November 2002
Shape-persistent macrocyclic aromatic tetrasulfonamides: Molecules with nanosized cavities and their nanotubular assemblies in solid state journal July 2006
Reverse osmosis molecular differentiation of organic liquids using carbon molecular sieve membranes journal August 2016
3D printed polyamide membranes for desalination journal August 2018
Design Considerations for Artificial Water Channel–Based Membranes journal July 2018