Increased structural complexity leads to higher activity: peptides as efficient and versatile catalysts for asymmetric aldol reactions.
[reaction: see text] Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions: (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catalysts can be changed from (R)- to (S)-selectivity by simple modifications of the secondary structure.
Krattiger
Philipp
P
Department of Chemistry, University of Basel, St. Johanns Ring 19, CH-4056 Basel, Switzerland.
Kovasy
Roman
R
Revell
Jefferson D
JD
Ivan
Stanislav
S
Wennemers
Helma
H
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000447:Aldehydes; D000588:Amines; D010455:Peptides; C116609:3-hydroxybutanal; D011392:Proline