Synthesis of Branched-Chain Sugars with a DHAP-Dependent Aldolase: Ketones are Electrophile Substrates of Rhamnulose-1-phosphate Aldolases
نویسندگان
چکیده
منابع مشابه
L - rhamnulose - 1 - phosphate and L - fuculose - 1 - phosphate aldolases mediated multi - enzyme cascade systems for
One-pot multistep stereoselective cascade reactions were implemented for the straightforward synthesis of various nitrocyclitols. Two kinases, an aldolase and a phosphatase were involved in this process together with a spontaneous intramolecular Henry reaction to provide a nitrocyclitol moiety. The C-C bond formation catalyzed by the aldolase and the nitroaldol reaction were key steps to build ...
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 کاملSynthesis of Sugars by Aldolase-Catalyzed, Condensation Reactionsl
Dihydroxyacetone phosphate was prepared in 2OGmmol scale from dihydroxyacetone by two procedures: reaction with phosphorus oxytrichloride and glycerol kinase catalyzed phosphorylation using ATP with in situ regeneration of ATP by phosphoenolp5rruvate or acetyl phosphate. Dihydroxyacetone phosphate was converted to fructose 6-phosphate in 80% yield by exposure to a mixture of co-immobilized trio...
متن کاملStructure of a Class I Tagatose-1,6-biphosphate Aldolase :
Tagatose-1,6-biphosphate (TBP) aldolase from Streptococcus pyogenes is a class I aldolase that exhibits a remarkable lack of chiral discrimination with respect to the configuration of hydroxyl groups at both C3 and C4 positions. The enzyme catalyzes the reversible cleavage of four diastereoisomers: fructose-1,6-bisphosphate (FBP), psicose-1,6-bis-phosphate, sorbose-1,6bisphosphate and tagatose-...
متن کاملEnzymes for carbohydrate and peptide syntheses
New practical procedures have been developed for the enzyme-catalyzed synthesis of carbohydrates and peptides. Aldolases have been shown to be effective catalysts for the synthesis of uncommon sugars, particularly azasugars. Enzymatic methods for the large-scale synthesis of oligosaccharides have been developed with the use of glycosyltransferases coupled with the regeneration of sugar nucleoti...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2018
ISSN: 1433-7851
DOI: 10.1002/anie.201712851