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• W1976144128 endingPage "8573" @default.
• W1976144128 startingPage "8565" @default.
• W1976144128 abstract "Among the proteinogenic amino acids, only proline is a secondary amine and only proline has a saturated ring. Electronegative substituents on C-4 (that is, Cγ) have a substantial effect on the trans/cis ratio of the prolyl peptide bond and the pucker of the pyrrolidine ring. 2-Azabicyclo[2.1.1]hexane is, in essence, a proline analogue with two Cγ atoms, one in each of the two prevalent ring puckers of proline. Here, 2-azabicyclo[2.1.1]hexane analogues of 2S-proline, (2S,4S)-4-hydroxyproline, and (2S,4S)-4-fluoroproline residues were synthesized, and their trans/cis ratios were shown to be invariant in a particular solvent. Thus, the substitution of a proline residue on C-4 affects the trans/cis ratio by altering the pucker of its pyrrolidine ring. This finding has implications for the conformation of collagen, which has an abundance of 2S-proline and (2S,4R)-4-hydroxyproline residues, and can be stabilized by (2S,4R)-4-fluoroproline and (2S,4S)-4-fluoroproline residues." @default.
• W1976144128 created "2016-06-24" @default.
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• W1976144128 date "2004-08-28" @default.
• W1976144128 modified "2023-10-11" @default.
• W1976144128 title "Substituted 2-Azabicyclo[2.1.1]hexanes as Constrained Proline Analogues: Implications for Collagen Stability" @default.
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• W1976144128 doi "https://doi.org/10.1021/jo049242y" @default.
• W1976144128 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15575731" @default.
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