109270-76-0

Upstream product

• 41527-39-3 dimethyl (2E)-pent-2-enedioate 
• 100-46-9 benzylamine 
• 115584-41-3 dimethyl 3-(benzylamino)pent-2-enedioate 
• 5164-76-1 dimethyl glutaconate 

Downstream Products

• 76144-16-6 5-methyl 1-hydrogen (S)-3-benzylaminoglutarate 
• 496881-80-2 methyl (S)-(-)-3-(benzylamino)-4-carbamoylbutanoate 
• 1034082-96-6 2-(N-benzylamino)pentane-1,5-diol 
• 496881-81-3 methyl (S)-(-)-3-[(N-benzyl-N-benzyloxycarbonyl)amino]-4-carbamoylbutanoate 
• 866752-08-1 3-(toluene-4-sulfonylamino)-pentanedioic acid 
• 838906-53-9 3-(toluene-4-sulfonylamino)-pentanedioic acid dimethyl ester 
• 838906-38-0 meso-4-(p-toluenesulfonamide)glutaric anhydride 

Relevant academic research and scientific papers

Iminodipropionic Acid as the Leaving Group for DNA Polymerization by HIV-1 Reverse Transcriptase

Previous studies have demonstrated that some selected amino monoacids and amino diacids can function as leaving groups in the polymerase-catalyzed incorporation of deoxynucleotides into DNA. Among these, the iminodiacetic acid phosphoramidate of deoxyadenosine monophosphate (IDA-dAMP) represents an interesting example, as it could overcome some of the problems observed when using L-aspartic acid as the leaving group, that is, poor chain elongation. We have now synthesized and evaluated a series of IDA-dAMP analogues that bear either an extended aliphatic chain in the amino acid function, or a phosphonic acid moiety (substituting for the carboxylic acid function). Among these compounds, the nucleotide with an iminodipropionic acid leaving group (IDP-dAMP) was identified as the best substrate; the excellent single incorporation (91% conversion to a P+1 strand at 50 μM) was at a substrate concentration ten times lower than that used for IDA-dAMP). This nucleotide also presented improved kinetics and elongation capability compared to IDA-dAMP. The analogues with T, G, and C base moieties were also investigated for their incorporation ability with HIV-1 RT. The incorporation efficiency was found to decrease in the order A>T>G>C. The properties of the iminodipropionic acid as the leaving group surpass those of previously evaluated leaving groups; this acid will be a prime candidate for in vivo testing.

Compounds and methods for amino-alkylenediol synthesis

A method of making an amino-alkylenediol and intermediate compounds useful in the method is disclosed. The method includes preparing a first intermediate compound comprising an aminoalkylene diol wherein a protecting group is linked to the amino functionality, and optionally, preparing a second intermediate compound comprising a salt of the first intermediate compound. The first intermediate compound has the structure wherein R is a divalent alkylene radical having from 2 to 20 carbon atoms, X and Y are independently a divalent linking moiety or a single bond, and Z is a protecting group. The second intermediate compound has the structure wherein R is a divalent alkylene radical having from 2 to 20 carbon atoms, X and Y are independently a divalent linking moiety or a single bond, TsO? is toluene sulfonate, and Z is a protecting group.

Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents

A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.

Synthesis of (R)-3,4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino)glutarate through enzymatic ammonolysis

Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].