Diastereoselectivity (enantioselectivity) of aldol condensations catalyzed by rabbit muscle aldolase at C-2 of RCHOHCHO if R has an appropriately placed negatively charged group
                                
                                    
                                        作者:Watson J. Lees、George M. Whitesides                                    
                                    
                                        DOI:10.1021/jo00059a047
                                    
                                    
                                        日期:1993.3
                                    
                                    D-Fructose 1,6-bis(phosphate) aldolase from rabbit muscle (RAMA, E.C. 4.1.2.13) catalyzes the aldol condensation between dihydroxyacetone phosphate (DHAP) and various aldehydes; the products are ketosugars with 3(S),4(R) stereochemistry. When racemic alpha-hydroxy aldehydes are condensed with DHAP, two diastereomeric products are formed. This paper demonstrates that RAMA can kinetically resolve alpha-hydroxy aldehydes with a negative charge removed four or five atoms from the aldehydic center. Kinetic resolution of either uncharged alpha-hydroxy aldehydes, or of alpha-hydroxy aldehydes with a negative charge removed three or seven atoms from the aldehydic carbon, is generally not as successful.