Conformational controlviasequence for a heteropeptoid in water: coupled NMR and Rosetta modelling

Trideep Rajale; Jacob C. Miner; Ryszard Michalczyk; M. Lisa Phipps; Jurgen G. Schmidt; Robert D. Gilbertson; Robert F. Williams; Charlie E.M. Strauss; Jennifer S. Martinez

doi:10.1039/d1cc01992a

Conformational controlviasequence for a heteropeptoid in water: coupled NMR and Rosetta modelling

Trideep Rajale, Jacob C. Miner, Ryszard Michalczyk, M. Lisa Phipps, Jurgen G. Schmidt, Robert D. Gilbertson, Robert F. Williams, Charlie E.M. Strauss, Jennifer S. Martinez

Applied Physics and Materials Science

Research output: Contribution to journal › Article › peer-review

Abstract

We report a critical advance in the generation and characterization of peptoid hetero-oligomers. A library of sub-monomers with amine and carboxylate side-chains are combined in different sequences using microwave-assisted synthesis. Their sequence-structure propensity is confirmed by circular dichroism, and conformer subtypes are enumerated by NMR. Biasing theψ-angle backbone totrans(180°) in Monte Carlo modelling favorsitoi+ 3 naphthyl-naphthyl stacking, and matches experimental ensemble distributions. Taken together, high-yield synthesis of heterooligomers and NMR with structure prediction enables rapid determination of sequences that induce secondary structural propensities for predictive design of hydrophilic peptidomimetic foldamers and their future libraries.

Original language	English (US)
Pages (from-to)	9922-9925
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	77
DOIs	https://doi.org/10.1039/d1cc01992a
State	Published - Oct 4 2021

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
General Chemistry
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Catalysis

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10.1039/d1cc01992a

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title = "Conformational controlviasequence for a heteropeptoid in water: coupled NMR and Rosetta modelling",

abstract = "We report a critical advance in the generation and characterization of peptoid hetero-oligomers. A library of sub-monomers with amine and carboxylate side-chains are combined in different sequences using microwave-assisted synthesis. Their sequence-structure propensity is confirmed by circular dichroism, and conformer subtypes are enumerated by NMR. Biasing theψ-angle backbone totrans(180°) in Monte Carlo modelling favorsitoi+ 3 naphthyl-naphthyl stacking, and matches experimental ensemble distributions. Taken together, high-yield synthesis of heterooligomers and NMR with structure prediction enables rapid determination of sequences that induce secondary structural propensities for predictive design of hydrophilic peptidomimetic foldamers and their future libraries.",

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T2 - coupled NMR and Rosetta modelling

AU - Rajale, Trideep

AU - Miner, Jacob C.

AU - Michalczyk, Ryszard

AU - Phipps, M. Lisa

AU - Schmidt, Jurgen G.

AU - Gilbertson, Robert D.

AU - Williams, Robert F.

AU - Strauss, Charlie E.M.

AU - Martinez, Jennifer S.

PY - 2021/10/4

Y1 - 2021/10/4

N2 - We report a critical advance in the generation and characterization of peptoid hetero-oligomers. A library of sub-monomers with amine and carboxylate side-chains are combined in different sequences using microwave-assisted synthesis. Their sequence-structure propensity is confirmed by circular dichroism, and conformer subtypes are enumerated by NMR. Biasing theψ-angle backbone totrans(180°) in Monte Carlo modelling favorsitoi+ 3 naphthyl-naphthyl stacking, and matches experimental ensemble distributions. Taken together, high-yield synthesis of heterooligomers and NMR with structure prediction enables rapid determination of sequences that induce secondary structural propensities for predictive design of hydrophilic peptidomimetic foldamers and their future libraries.

AB - We report a critical advance in the generation and characterization of peptoid hetero-oligomers. A library of sub-monomers with amine and carboxylate side-chains are combined in different sequences using microwave-assisted synthesis. Their sequence-structure propensity is confirmed by circular dichroism, and conformer subtypes are enumerated by NMR. Biasing theψ-angle backbone totrans(180°) in Monte Carlo modelling favorsitoi+ 3 naphthyl-naphthyl stacking, and matches experimental ensemble distributions. Taken together, high-yield synthesis of heterooligomers and NMR with structure prediction enables rapid determination of sequences that induce secondary structural propensities for predictive design of hydrophilic peptidomimetic foldamers and their future libraries.

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Conformational controlviasequence for a heteropeptoid in water: coupled NMR and Rosetta modelling

Abstract

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