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• W2091470384 abstract "4(S)-Hydroxyproline (Hyp) residues constitute about l0%, of most forms of collagen, the most abundant protein in vertebrates. X-Ray diffraction analysis was used to ascertain how the structure of proline residues is affected by the inductive effect elicited by the hydroxyl group of Hyp residues. N-Acetylproline methylester (1), N-acetyl-4(S)-hydroxyproline methylester (2) and N-acetyl-4(S)-fluoroproline methylester (3) were synthesized, and their crystalline structures were determined at high resolution. The amide bond of crystalline 1 was in the cis conformation. which is the minor isomer in solution, and the pyrrolidine ring of 1 had Cγ-endo pucker. In crystalline 2 and 3 the arnide bonds were in the trans conformation, and the pyrrolidine rings had Cγ-exo pucker. The lengths of the bonds between sp3-hybridized carbon atoms in the pyrrolidine ring were significantly shorter in 2 and 3 than in 1, as was predicted by ab initio molecular orbital calculations at the RHF/3-21G level of theory. No significant change in bond length was observed in the other bonds of 1, 2 or 3. The pyramidylization of the nitrogen atom increased dramatically in the order: 1<2<3. Together, these results indicate that electron-withdrawing substituents in the 4-position of proline residues can have a significant influence on the structure of these residues. In particular, the change in pyramidylization suggests that such substituents increase the sp3-character of the prolyl nitrogen atom and could thereby alter the rate of prolyl peptide bond isomerization." @default.
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• W2091470384 date "2009-01-12" @default.
• W2091470384 modified "2023-10-18" @default.
• W2091470384 title "Inductive effects on the structure of proline residues" @default.
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• W2091470384 doi "https://doi.org/10.1111/j.1399-3011.1994.tb00169.x" @default.
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