Substituted 2-Azabicyclo[2.1.1]hexanes as Constrained Proline Analogues: Implications for Collagen Stability.
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چکیده
منابع مشابه
Substituted 2-azabicyclo[2.1.1]hexanes as constrained proline analogues: implications for collagen stability.
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, C(gamma)) 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 C(gamma) atoms, one in each of the two preval...
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7-Azabicyclo[2.2.1]heptane-2-carboxylic acid 11 was prepared in enantiopure form, and its catalytic potential in the direct aldol reaction between acetone and 4-nitrobenzaldehyde was assessed. The bicyclic system was found to be more selective than its monocyclic analogue beta-proline 5b. A comparative density functional theory study of proline 1, beta-proline 5b, and 11 in the latter reaction ...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2006
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo052444p