Gram scale synthesis of 3-fluoro-1-hydroxyacetone phosphate: a novel donor substrate in rabbit muscle aldolase-catalyzed aldol reactions.
نویسندگان
چکیده
An efficient gram scale synthesis of 3-fluoro-1-hydroxyacetone phosphate (FHAP) has been developed. As a close analog to dihydroxyacetone phosphate, FHAP was used as a novel donor substrate for rabbit muscle aldolase catalyzed reactions. The different binding affinities of the gem-diol and keto form of FHAP were studied by (19)F-NMR.
منابع مشابه
Aldolase Antibodies of Remarkable Scope
This paper describes the substrate specificity, synthetic scope, and efficiency of aldolase catalytic antibodies 38C2 and 33F12. These antibodies use the enamine mechanism common to the natural Class I aldolase enzymes. Substrates for these catalysts, 23 donors and 16 acceptors, have been identified. The aldol acceptor specificity is expected to be much broader than that defined here since all ...
متن کاملHighly efficient aldol additions of DHA and DHAP to N-Cbz-amino aldehydes catalyzed by L-rhamnulose-1-phosphate and L-fuculose-1-phosphate aldolases in aqueous borate buffer.
Aldol addition reactions of dihydroxyacetone (DHA) to N-Cbz-amino aldehydes catalyzed by L-rhamnulose-1-phosphate aldolase (RhuA) in the presence of borate buffer are reported. High yields of aldol adduct (e.g. 70-90%) were achieved with excellent (>98 : 2 syn/anti) stereoselectivity for most S or R configured acceptors, which compares favorably to the reactions performed with DHAP. The stereoc...
متن کاملA Novel Convenient Preparation of Dihydroxyacetone Phosphate and Its Use in Enzymatic Aldol Reactions
A new preparation of the stable barium salt of 2,5-bis(phosphonooxymethvl)-2.5-diethoxv-1.4-dioxane Ba-2 is described, which bv treatment with DOWEX 50 B+ gives dihydroxyacetone ph&phate (DHAP) in high yield. DHAP prepared by this method was used for aldolase-catalyzed condensations. An increasing number of papers dealing with enzymatic aldol reactions demonstrates their synthetic utility 1,2,4...
متن کاملInteraction between rabbit muscle aldolase and dihydroxyacetone phosphate.
It is generally accepted that the mechanism of enzyme activity includes a combination of enzyme and substrate. This concept forms the basis for the conventional kinetic analyses of enzymatic reactions (1). Direct evidence for the existence of enzyme-substrate combinations is as yet meager. The binding of pyridine nucleotide coenzymes as substrates to various dehydrogenases has been shown to res...
متن کاملDirect catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti-Mannich and syn-aldol reactions.
Chiral 1,2-amino alcohols and 1,2-diols are common structural motifs found in a vast array of natural and biologically active molecules.1 Recently, significant efforts have been applied toward the development of direct catalytic asymmetric approaches to the construction of these units based on the addition of unmodified R-hydroxyketones to imines or aldehydes in Mannich-type and aldol reactions...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 47 23 شماره
صفحات -
تاریخ انتشار 2011