Self-Sorting in Diastereomeric Mixtures of Functionalized Dipeptides

Qingwen Guan; Kate McAulay; Tian Xu; Sarah E. Rogers; Charlotte Edwards-Gayle; Ralf Schweins; Honggang Cui; Annela M. Seddon; Dave J. Adams

doi:10.1021/acs.biomac.3c00246

Self-Sorting in Diastereomeric Mixtures of Functionalized Dipeptides

Qingwen Guan
, Kate McAulay
, Tian Xu
, Sarah E. Rogers
, Charlotte Edwards-Gayle
, Ralf Schweins
, Honggang Cui
, Annela M. Seddon
, Dave J. Adams^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

9 Citations (Scopus)

Abstract

Self-sorting in functionalized dipeptide systems can be driven by the chirality of a single amino acid, both at a high pH in the micellar state and at a low pH in the gel state. The structures formed are affected to some degree by the relative concentrations of each component showing the complexity of such an approach. The structures underpinning the gel network are predefined by the micellar structures at a high pH. Here, we describe the systems prepared from two dipeptide-based gelators that differ only by the chirality of one of the amino acids. We provide firm evidence for self-sorting in the micellar and gel phases using small-angle neutron scattering and cryo-transmission electron microscopy (cryo-TEM), showing that complete self-sorting occurs across a range of relative concentrations.

Original language	English
Pages (from-to)	2847-2855
Number of pages	9
Journal	Biomacromolecules
Volume	24
Issue number	6
DOIs	https://doi.org/10.1021/acs.biomac.3c00246
Publication status	Published - 12 Jun 2023

Bibliographical note

Funding Information:
Q.G. thanks the China Scholarship Council (grant no. 202006440011) for funding. D.A. thanks the EPSRC for a Fellowship (L/021978/2) which also funded K.M. The authors acknowledge STFC beamtime allocation 1820016 on SANS2D at ISIS Neutron and Muon Source, Didcot, U.K., DOI: 10.5286/ISIS.E.RB 1820016 and beamtime allocation. They also acknowledge STFC beamtime allocation SM29985 on B21 at Diamond. The experiment at the Institut Laue Langevin was allocated beamtime under experiment number 9-10-1304 (DOI: 10.5291/ILL-DATA.9-10-1304). This work benefited from SasView software, originally developed by the DANSE project under NSF award DMR-0520547. The authors thank Dan McDowall and Simona Bianco (University of Glasgow) for help in running the SAXS samples.

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.

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title = "Self-Sorting in Diastereomeric Mixtures of Functionalized Dipeptides",

abstract = "Self-sorting in functionalized dipeptide systems can be driven by the chirality of a single amino acid, both at a high pH in the micellar state and at a low pH in the gel state. The structures formed are affected to some degree by the relative concentrations of each component showing the complexity of such an approach. The structures underpinning the gel network are predefined by the micellar structures at a high pH. Here, we describe the systems prepared from two dipeptide-based gelators that differ only by the chirality of one of the amino acids. We provide firm evidence for self-sorting in the micellar and gel phases using small-angle neutron scattering and cryo-transmission electron microscopy (cryo-TEM), showing that complete self-sorting occurs across a range of relative concentrations.",

author = "Qingwen Guan and Kate McAulay and Tian Xu and Rogers, \{Sarah E.\} and Charlotte Edwards-Gayle and Ralf Schweins and Honggang Cui and Seddon, \{Annela M.\} and Adams, \{Dave J.\}",

note = "Funding Information: Q.G. thanks the China Scholarship Council (grant no. 202006440011) for funding. D.A. thanks the EPSRC for a Fellowship (L/021978/2) which also funded K.M. The authors acknowledge STFC beamtime allocation 1820016 on SANS2D at ISIS Neutron and Muon Source, Didcot, U.K., DOI: 10.5286/ISIS.E.RB 1820016 and beamtime allocation. They also acknowledge STFC beamtime allocation SM29985 on B21 at Diamond. The experiment at the Institut Laue Langevin was allocated beamtime under experiment number 9-10-1304 (DOI: 10.5291/ILL-DATA.9-10-1304). This work benefited from SasView software, originally developed by the DANSE project under NSF award DMR-0520547. The authors thank Dan McDowall and Simona Bianco (University of Glasgow) for help in running the SAXS samples. Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

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AU - Schweins, Ralf

AU - Cui, Honggang

AU - Seddon, Annela M.

AU - Adams, Dave J.

N1 - Funding Information: Q.G. thanks the China Scholarship Council (grant no. 202006440011) for funding. D.A. thanks the EPSRC for a Fellowship (L/021978/2) which also funded K.M. The authors acknowledge STFC beamtime allocation 1820016 on SANS2D at ISIS Neutron and Muon Source, Didcot, U.K., DOI: 10.5286/ISIS.E.RB 1820016 and beamtime allocation. They also acknowledge STFC beamtime allocation SM29985 on B21 at Diamond. The experiment at the Institut Laue Langevin was allocated beamtime under experiment number 9-10-1304 (DOI: 10.5291/ILL-DATA.9-10-1304). This work benefited from SasView software, originally developed by the DANSE project under NSF award DMR-0520547. The authors thank Dan McDowall and Simona Bianco (University of Glasgow) for help in running the SAXS samples. Publisher Copyright: © 2023 The Authors. Published by American Chemical Society.

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N2 - Self-sorting in functionalized dipeptide systems can be driven by the chirality of a single amino acid, both at a high pH in the micellar state and at a low pH in the gel state. The structures formed are affected to some degree by the relative concentrations of each component showing the complexity of such an approach. The structures underpinning the gel network are predefined by the micellar structures at a high pH. Here, we describe the systems prepared from two dipeptide-based gelators that differ only by the chirality of one of the amino acids. We provide firm evidence for self-sorting in the micellar and gel phases using small-angle neutron scattering and cryo-transmission electron microscopy (cryo-TEM), showing that complete self-sorting occurs across a range of relative concentrations.

AB - Self-sorting in functionalized dipeptide systems can be driven by the chirality of a single amino acid, both at a high pH in the micellar state and at a low pH in the gel state. The structures formed are affected to some degree by the relative concentrations of each component showing the complexity of such an approach. The structures underpinning the gel network are predefined by the micellar structures at a high pH. Here, we describe the systems prepared from two dipeptide-based gelators that differ only by the chirality of one of the amino acids. We provide firm evidence for self-sorting in the micellar and gel phases using small-angle neutron scattering and cryo-transmission electron microscopy (cryo-TEM), showing that complete self-sorting occurs across a range of relative concentrations.

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Self-Sorting in Diastereomeric Mixtures of Functionalized Dipeptides

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