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Stabilization of a miniprotein fold by an unpuckered proline surrogate

https://doi.org/10.1038/s42004-025-01474-6

Wright, Madison M; Rajewski, Benjamin H; Gerrein, Taylor A; Xu, Zhiyi; Smith, Lorna J; Seth_Horne, W; Del_Valle, Juan R (December 2025, Communications Chemistry)

Free, publicly-accessible full text available December 1, 2026
Synthesis and stability of collagen mimetic peptides featuring δ-heteroatom-substituted prolines

https://doi.org/10.1039/D5OB00176E

Gerrein, Taylor A; Wright, Madison M; Cano-Sampaio, Natalia; Del_Valle, Juan R (March 2025, Organic & Biomolecular Chemistry)

Substituting the central proline residue in a collagen mimetic peptide with δ-oxaproline affords a faster-folding analogue with equivalent triple helix stability.
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Free, publicly-accessible full text available March 26, 2026
N -Aminoglycine and Its Derivatives Stabilize PPII Secondary Structure

https://doi.org/10.1021/acs.orglett.3c01502

Rajewski, Benjamin H.; Wright, Madison M.; Gerrein, Taylor A.; Del Valle, Juan R. (June 2023, Organic Letters)

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Diastereoselective Synthesis of (3R,5R)-γ-Hydroxypiperazic Acid

https://doi.org/10.1055/s-0040-1719824

Gerrein, Taylor A.; Elbatrawi, Yassin M.; Del Valle, Juan R. (October 2021, Synlett)

Abstract We report an asymmetric synthesis of the (3R,5R)-γ-hydroxypiperazic acid (γ-OHPiz) residue encountered in several bioactive nonribosomal peptides. Our strategy relies on a diastereoselective enolate hydroxylation reaction and electrophilic N-amination to provide the acyclic γ-OHPiz precursor. This orthogonally protected α-hydrazino acid intermediate is amenable to late-stage diazinane ring formation following incorporation into a peptide chain. We determined the N-terminal amide rotamer propensity of the γ-OHPiz residue and showed that the γ-OH substituent enhances trans-amide bias relative to piperazic acid.
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