Boc- ß-HoIle-OH

Boc- ß-HoIle-OH

Efficient synthesis of (S)-N-Boc-3-hydroxypiperidine using an (R)-specific carbonyl reductase from Candida parapsilosis.[Pubmed:28243985]

World J Microbiol Biotechnol. 2017 Mar;33(3):61.

(S)-N-Boc-3-hydroxypiperidine (S-NBHP) is a critical chiral intermediate in the synthesis of pharmaceuticals, including ibrutinib, the active pharmaceutical ingredient of the new drug Imbruvica approved for the treatment of lymphoma. An (R)-specific carbonyl reductase from Candida parapsilosis (CprCR, also known as R-specific alcohol dehydrogenase) that catalyzes asymmetric reduction to produce (S)-N-Boc-3-hydroxypiperidine (S-NBHP) was identified for the first time. When co-expressed with a glucose dehydrogenase from Bacillus megaterium in Escherichia coli Rosetta (DE3), recombinant crude enzyme exhibited an activity of 9 U/mg with N-Boc-3-piperidone as the substrate and 12 U/mg with glucose as the substrate. The biocatalysis of N-Boc-3-piperidone to S-NBHP using recombinant whole-cell biocatalysts was processed in a water/butyl acetate system as well as an aqueous monophasic system without extra NAD(+)/NADH. This process showed great commercial potential, with a 100 g/l substrate concentration and a whole cells loading (w/v) of 10%, with the conversion of 97.8% and an e.e. of 99.8% in an aqueous monophasic system.

Tuning the Molar Composition of "Charge-Shifting" Cationic Copolymers Based on 2-(N,N-Dimethylamino)Ethyl Acrylate and 2-(tert-Boc-Amino)Ethyl Acrylate.[Pubmed:28045212]

Macromol Rapid Commun. 2017 Mar;38(5).

Copolymers of 2-(N,N-dimethylamino)ethyl acrylate (DMAEA) and 2-(tert-Boc-amino)ethyl acrylate (tBocAEA) are synthesized by reversible addition-fragmentation chain transfer polymerization in a controlled manner with defined molar masses and narrow molar masses distributions (Eth

Rhodium(III)-Catalyzed Ortho-Alkenylation of Anilines Directed by a Removable Boc-Protecting Group.[Pubmed:28322570]

Org Lett. 2017 Apr 7;19(7):1800-1803.

The rhodium(III)-catalyzed ortho-alkenylation of N-Boc-anilines with alkenes such as acrylate ester and styrene proceeds smoothly through C-H bond cleavage. Obtained o-alkenylanilines can be readily transformed to nitrogen-containing fused heteroaromatic compounds including indoles and quinolines.

Effects on Energy Metabolism of Two Guanidine Molecules, (Boc)2 -Creatine and Metformin.[Pubmed:28128472]

J Cell Biochem. 2017 Sep;118(9):2700-2711.

Several enzymes are involved in the energy production, becoming a possible target for new anti-cancer drugs. In this paper, we used biochemical and in silico studies to evaluate the effects of two guanidine molecules, (Boc)2 -creatine and metformin, on creatine kinase, an enzyme involved in the regulation of intracellular energy levels. Our results show that both drugs inhibit creatine kinase activity; however, (Boc)2 -creatine displays a competitive inhibition, while metformin acts with a non-competitive mechanism. Moreover, (Boc)2 -creatine is able to inhibit the activity of hexokinase with a non-competitive mechanism. Considering that creatine kinase and hexokinase are involved in energy metabolism, we evaluated the effects of (Boc)2 -creatine and metformin on the ATP/AMP ratio and on cellular proliferation in healthy fibroblasts, human breast cancer cells (MDA-MB-468), a human neuroblastoma cell line (SH-SY5Y), a human Hodgkin lymphoma cell line (KMH2). We found that healthy fibroblasts were only partially affected by (Boc)2 -creatine, while both ATP/AMP ratio and viability of the three cancer cell lines were significantly decreased. By inhibiting both creatine kinase and hexokinase, (Boc)2 -creatine appears as a promising new agent in anticancer treatment. Further research is needed to understand what types of cancer cells are most suitable to treatment by this new compound. J. Cell. Biochem. 118: 2700-2711, 2017. (c) 2017 Wiley Periodicals, Inc.