1-Deoxynojirimycin

1-Deoxynojirimycin.svg 135px (2R,3R,4R,5S)-2-(Hydroxymethyl)piperidine-3,4,5-triol 4642 19130-96-2 correct CAS correct FDA FZ56898FLE 29435 44369 D09605 C1[C@@H]([C@H]([C@@H]([C@H](N1)CO)O)O)O 27360 1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1 LXBIFEVIBLOUGU-JGWLITMVSA-N 6 13 1 4 195 1-Deoxynojirimycin (DNJ or 1-DNJ), also called duvoglustat or moranolin,KEGG: Deoxynojirimycin. is an alpha-glucosidase inhibitor, most commonly found in mulberry leaves. Although it can be obtained in small quantities by brewing an herbal tea from mulberry leaves, interest in commercial production has led to research on developing mulberry tea higher in DNJ,Chaluntorn Vichasilp Development of high 1-deoxynojirimycin (DNJ) content mulberry tea and use of response surface methodology to optimize tea-making conditions for highest DNJ extraction LWT - Food Science and Technology 2012 45 2 226–232 10.1016/j.lwt.2011.09.008 etal and on alternate routes of production, such as via Bacillus species.23265519 2013 Onose S Ikeda R Nakagawa K Kimura T Yamagishi K Higuchi O Miyazawa T Production of the α-glycosidase inhibitor 1-deoxynojirimycin from Bacillus species 138 1 516–23 10.1016/j.foodchem.2012.11.012 Food Chemistry Biosynthesis 1-Deoxynojirimycin is a polyhydroxylated piperidine alkaloid produced from D-Glucose in various plants, such as Commelina communis, and in the Streptomyces and Bacillus bacteria.Gomollon-Bel Fernando Delso Ignacio Tejero Tomas Merino Pedro 2014-11-12 Biosynthetic Pathways to Glycosidase Inhibitors Current Chemical Biology en 8 1 10–16 10.2174/221279680801141112094818 2212-7968 10261/122571 freeKang Kyung-Don Cho Yong Seok Song Ji Hye Park Young Shik Lee Jae Yeon Hwang Kyo Yeol Rhee Sang Ki Chung Ji Hyung Kwon Ohsuk June 2011 Identification of the genes involved in 1-deoxynojirimycin synthesis in Bacillus subtilis MORI 3K-85 The Journal of Microbiology en 49 3 431–440 10.1007/s12275-011-1238-3 21717329 24841974 1225-8873 High quantities of this iminosugar are produced in Bacillus subtilis, a process initiated by a TYB gene cluster composed of gabT1 (aminotransferase), yktc1 (phosphatase), and gutB1 (oxidoreductase).Kyung-Don Kang Cho Yong Seok Song Ji Hye Park Young Shik Lee Jae Yeon Hwang Kyo Yeol Rhee Sang Ki Chung Ji Hyung Kwon Ohsuk June 2011 Identification of the genes involved in 1-deoxynojirimycin synthesis in Bacillus subtilis MORI 3K-85 The Journal of Microbiology en 49 3 431–440 10.1007/s12275-011-1238-3 21717329 24841974 1225-8873Clark Lorraine F. Johnson Jodie V. Horenstein Nicole A. 2011-07-22 Identification of a Gene Cluster that Initiates Azasugar Biosynthesis in Bacillus amyloliquefaciens ChemBioChem en 12 14 2147–2150 10.1002/cbic.201100347 21786380 32186936 1439-4227 In Bacillus subtilis, D-glucose first undergoes glycolysis, opening the 6-member ring and producing fructose-6-phosphate.Jiang Peixia Mu Shanshan Li Heng Li Youhai Feng Congmin Jin Jian-Ming Tang Shuang-Yan 2015-02-24 Design and Application of a Novel High-throughput Screening Technique for 1-Deoxynojirimycin Scientific Reports En 5 1 8563 10.1038/srep08563 free 2045-2322 4338435 25708517 2015NatSR...5E8563J GabT1 catalyzes transamination at the C2 position, followed by a dephosphorylation by the Yktc1 enzyme, resulting in 2-amino-2-deoxy-D-mannitol (ADM), an essential precursor. Regio-selective oxidation by GutB1 occurs at the exposed C6 hydroxyl of ADM, pushing a C2-N-C6 cyclization of the resulting 6-oxo intermediate,Onose Shinji Ikeda Ryoichi Nakagawa Kiyotaka Kimura Toshiyuki Yamagishi Kenji Higuchi Ohki Miyazawa Teruo May 2013 Production of the α-glycosidase inhibitor 1-deoxynojirimycin from Bacillus species Food Chemistry 138 1 516–523 10.1016/j.foodchem.2012.11.012 23265519 0308-8146 creating manojirimycin (MJ). Epimerization of MJ at the C2 position yields the nojirimycin isomer. Nojirimycin is then dehydrated (loss of -OH at C1 position), along with reduction of the imine moiety. This results in the product 1-DNJ. thumb|left|500px|Biosynthesis of 1-deoxynojirimycin in Bacillus subtilis Pathway variations In the Streptomyces subrutilus species, a secondary pathway branching from the manojirimycin precursor results in 1-deoxymanojirimycin via dehydration and reduction of the isomer. However, Bacillus subtilis does not produce 1-deoxymanojirimycin despite the presence of the manojirimycin precursor. Iminosugar biosynthesis in Commelina communis involves C1-C5 cyclisation of the original D-glucose precursor without the subsequent inversion. See also Nojirimycin 1-Deoxygalactonojirimycin, a stereoisomer of 1-deoxynojirimycin References Category:Iminosugars