Brunner, Henri and Tsuno, Takashi (2019) Selective distortion of the planar group C alpha C'(O)O to a chiral flat tetrahedron in the amino acid alanine. CHIRALITY, 31 (9). pp. 628-634. ISSN 0899-0042, 1520-636X
Full text not available from this repository. (Request a copy)Abstract
Based on a Cambridge Structural Database (CSD) search, a meta-analysis of 116 structures of alanine H3NC alpha H(CH3)C '(O)O and its derivatives H3NC alpha H(CH3)C '(O)O(H/R/M), protonated, esterified, or coordinated at the carboxylic group, shows that in the first step of a chirality chain, the L configuration at C-alpha induces (M) and (P) conformations with respect to rotation around the central C ' C-alpha bond. In the second step, the (M) and (P) conformations selectively distort the planar carboxylic group C alpha C'(O-cis)O-trans to asymmetric flat (R) and (S) tetrahedra. High diastereoselectivities are caused by the two players attraction N horizontal ellipsis O-cis and repulsion O-trans horizontal ellipsis C-Me, which work together in (L,M,R) configurations but against each other in (L,P,S) configurations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; alanine; chirality; conformation; diastereoselectivity; pyramidalization |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 Apr 2020 08:12 |
| Last Modified: | 07 Apr 2020 08:12 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26612 |
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