Enzyme-Based Organic Synthesis. Cheanyeh Cheng

Enzyme-Based Organic Synthesis - Cheanyeh Cheng


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href="#fb3_img_img_e8958d95-ccc0-5b3a-985a-f828aa3692ae.gif" alt="Chemical reaction depicting the transfer of gamma-phosphoryl group from ATP to hydroxyl group containing substrates by kinases."/>

      Source: Chapman and Wong [41].

      Protein crystallography in the solid state and 19F NMR in solution have elucidated the formation of a trigonal bipyramidal transition state with phosphorus fully bonded to three equatorial oxygens and partially bonded to axial donor’s oxygen and acceptor’s oxygen [43]. The hydrolysis of ATP to form ADP and Pi is highly exergonic that is used to drive the synthesis of information‐rich macromolecules, the transport of solute across membranes, and motion produced by muscle contraction.

Chemical reaction depicting phosphorylation of 4HT to 4PHT by kinase DUF1537 for enzyme cofactor PLP biosynthesis.

      Source: Modified from Thiaville et al. [44].

Chemical reaction depicting sequential phosphorylation of peptide R-SSD3 with casein kinases.

Chemical reaction depicting synthetic pathway of melatonin from serotonin by two kinds of acetyltransferases.

      Source: Based on Tan et al. [48]; Weissbach and Redfield [49]; Axelrod and Weissbach [50].

      The GCN5‐related N‐acetyltransferase (GNAT) superfamily encompasses more than 10 000 related enzymes in all kingdoms of life and human acetyl‐CoA: glucosamine‐6‐phosphate N‐acetyltransferase 1 (GNA1) belongs to a member of it [54, 55]. In the cytosol, GNA1 catalyzes the transfer of an acetyl group from the acetyl coenzyme A donor substrate to the acceptor substrate glucosamine‐6‐phosphate (GlcN6P) to form N‐acetyl‐glucosamine‐6‐phosphate (GlcNAc6P) that is used as an intermediate in the biosynthesis of UDP‐GlcNAc. Since N‐butyryl glucosamine (GlcNBu), an analog of GlcNAc, has been shown the healing properties of bone and articular cartilage in animal’s arthritis, enzymatic synthesis of GlcNBu is important for biomedical applications [56–58]. Research results have shown that both acetyl and n‐butyl groups were transferred to GlcN6P by GNA1 to form corresponding GlcNAc6P and GlcNBu6P, respectively [54]. Therefore, GlcNBu6P can be easily and subsequently converted to GlcNBu by alkaline phosphatase.


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