Conformational control via sequence for a heteropeptoid in water: coupled NMR and Rosetta modelling. Issue 77 (9th September 2021)

• Record Type: Journal Article
• Authors: Rajale, Trideep; Miner, Jacob C.; Michalczyk, Ryszard; Phipps, M. Lisa; Schmidt, Jurgen G.; Gilbertson, Robert D.; Williams, Robert F.; Strauss, Charlie E. M.; Martinez, Jennifer S.
• Is Part Of: Chemical communications. Volume 57:Issue 77(2021)
• Page Start: 9922
• Page End: 9925
• Publication Date: 2021-09-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc01992a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Structured water-soluble and hetero-oligomeric peptoids: the importance of peptoid-specific backbone restrictions. 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 the ψ -angle backbone to trans (180°) in Monte Carlo modelling favors i to i + 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.