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- W2000463078 abstract "The 1H NMR spectral changes observed at 300 MHz during titration in D2O of cis-D-allohydroxyproline (aHyp) allow to define the approximate ring conformation in solution and the rotational behaviour of the carboxyl around Cα-C′. The cationic species is characterized by ring conformers close to the envelopes with Cγ-endo and Cδ-exo as the flap. The carboxyl plane is in the direction of Cδ/Cγ (Ψ = 60-90°), allowing for an interaction with the quasi-axial γ-OD. During titration of the carboxylic group this plane rotates nearer to γ-OD. The latter picture is consistent with observations reported in the literature for the behaviour in Pro and trans-Hyp2, 4. When the amine function is titrated (pD > 10) the carboxylate group becomes coplanar with D-N-Cα (Ψ ∼ 0°). In conjunction the ring escapes into a form best defined by a twist having Cδ exo and N endo. The possibility for intramolecular hydrogen bonding (e.g. between the carboxylic group and the hydroxyl function in the cation and zwitterion or between the same group on the amine function in the anion) contributes little to the inherent pyrrolidine ring conformation, although a restriction of conformational freedom to δ+ in D2O for the zwitterionic state could be revealed by comparison to DMSO-d6, where concomitantly the γ− form also is present." @default.
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- W2000463078 date "2010-09-01" @default.
- W2000463078 modified "2023-10-18" @default.
- W2000463078 title "A Re-Investigation of the Conformational Behaviour of CIS-D-Allo-Hydroxyproline in Solution" @default.
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- W2000463078 doi "https://doi.org/10.1002/bscb.19790880305" @default.
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