1-Deoxynojirimycin - Explore the Science & Experts | ideXlab

Scan Science and Technology

Contact Leading Edge Experts & Companies

1-Deoxynojirimycin

The Experts below are selected from a list of 321 Experts worldwide ranked by ideXlab platform

Naoki Asano – 1st expert on this subject based on the ideXlab platform

  • α-1-C-Alkyl-1-Deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile
    Bioorganic & Medicinal Chemistry Letters, 2004
    Co-Authors: Guillaume Godin, Philippe Compain, Olivier R. Martin, Kyoko Ikeda, Liang Yu, Naoki Asano

    Abstract:

    : A series of alpha- and beta-1-C-alkyl-1-Deoxynojirimycin derivatives was prepared and evaluated as glycosidase inhibitors. Biological assays showed a marked dependence of the selectivity and potency of the inhibitors upon the position of the alkyl chain (alpha-1-C-, beta-1-C- or N-alkyl derivatives). In addition, the efficiency of alpha-1-C-alkyl-1-Deoxynojirimycin derivatives as intestinal isomaltase inhibitors increases with the length of the alkyl chain. The strongest inhibition was found for alpha-1-C -nonyl-1-Deoxynojirimycin with an IC50=3.5 nM (25x more potent inhibitor than the shorter chain homologue carrying a C8 chain). These results demonstrate that subtle changes in the aglycon fragment may result in remarkable enzyme specificity.

  • polyhydroxylated alkaloids isolated from mulberry trees morus alba l and silkworms bombyx mori l
    Journal of Agricultural and Food Chemistry, 2001
    Co-Authors: Naoki Asano, Haruhisa Kizu, Kyoko Ikeda, Toru Yamashita, Kayo Yasuda, Yukihiko Kameda, Atsushi Kato, Robert J Nash

    Abstract:

    New polyhydroxylated alkaloids, (2R,3R,4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine-N-propionamide from the root bark of Morus alba L., and 4-O-α-d-galactopyranosyl-calystegine B2 and 3β,6β-dihydroxynortropane from the fruits, were isolated by column chromatography using a variety of ion-exchange resins. Fifteen other polyhydroxylated alkaloids were also isolated. 1-Deoxynojirimycin, a potent α-glucosidase inhibitor, was concentrated 2.7-fold by silkworms feeding on mulberry leaves. Some alkaloids contained in mulberry leaves were potent inhibitors of mammalian digestive glycosidases but not inhibitors of silkworm midgut glycosidases, suggesting that the silkworm has enzymes specially adapted to enable it to feed on mulberry leaves. The possibility of preventing the onset of diabetes and obesity using natural dietary supplements containing 1-Deoxynojirimycin and other α-glucosidase inhibitors in high concentration is of great potential interest. Keywords: Morus alba; Bombyx mori; polyhydroxylated alkaloid…

  • n containing sugars from morus alba and their glycosidase inhibitory activities
    Carbohydrate Research, 1994
    Co-Authors: Naoki Asano, Kengo Oseki, Emiko Tomioka, Haruhisa Kizu, Katsuhiko Matsui

    Abstract:

    Abstract The reexamination of N -containing sugars from the roots of Morus alba by improved purification procedures led to the isolation of eighteen N -containing sugars, including seven that were isolated from the leaves of Morus bombycis . These N -containing sugars are 1-Deoxynojirimycin ( 1 ), N -methyl-1-Deoxynojirimycin ( 2 ), fagomine ( 3 ), 3- epi -fagomine ( 4 ), 1,4-dideoxy-1,4-imino-pD-arabinitol ( 5 ), 1,4-dideoxy-1,4-imino-pD-ribitol ( 6 ), calystegin B 2 (1α,2β,3α,4β-tetrahydroxy- nor -tropane, 7 ), calystegin C 1 , (1α,2β,3α,6α-pentahydroxy- nor -tropane, 8 ), 1,4-dideoxy-1,4-imino-(2- O -β-pD-glucopyranosyl)- d -glucopyranosyl)- d -arabinitol ( 9 ), and nine glycosides of 1 . These glycosides consist of 2- O – and 6- O -α- d -galactopyranosyl-1-Deoxynojirimycins ( 10 and 11 , respectively), 2- O -, 3- O – and 4- O -α- d -glucopyranosyl-1-Deoxynojirimycins ( 12 , 13 , and 14 , respectively), and 2- O -, 3- O -, 4- O – and 6- O -β- D -glucopyranosyl-1-Deoxynojirimycins ( 15 , 16 , 17 , and 18 , respectively). Compound 4 is a new member of polyhydroxylated piperidine alkaloids, and the isolation of 6 is the first report of its natural occurrence. It has recently been found that the polyhydroxy- nor -tropane alkaloids possess potent glycosidase inhibitory activities. Calystegin A 3 is the trihydroxy- nor -tropane, and calystegins B 1 and B 2 are the tetrahydroxy- nor -tropane. Calystegin C 1 , a new member of calystegins, is the first naturally occurring pentahydroxy- nor -tropane alkaloid. The inhibitory activities of these compounds are investigated against rat digestive glycosidases and various commercially available glycosidases.

Herman S. Overkleeft – 2nd expert on this subject based on the ideXlab platform

  • Synthesis of glycosylated 1-Deoxynojirimycins starting from natural and synthetic disaccharides
    European Journal of Organic Chemistry, 2018
    Co-Authors: Jeanine Van Mechelen, Adrianus M C H Van Den Nieuwendijk, Richard J B H N Van Den Berg, Gijsbert A Van Der Marel, Johannes M F G Aerts, Jeroen D. C. Codée, Herman S. Overkleeft

    Abstract:

    Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1‐deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1‐deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

  • synthesis of eight 1 deoxynojirimycin isomers from a single chiral cyanohydrin
    European Journal of Organic Chemistry, 2012
    Co-Authors: Adrianus M C H Van Den Nieuwendijk, Richard J B H N Van Den Berg, Mark Ruben, Martin D. Witte, Johannes Brussee, Rene G A Boot, Gijsbert A Van Der Marel, Johannes M F G Aerts, Herman S. Overkleeft

    Abstract:

    Eight configurational 1-Deoxynojirimycin isomers have been synthesized starting from a chiral cyanohydrin as the common precursor. The cyanohydrin chiral pool building block is easily accessible in large quantities by using almond hydroxynitrile lyase as the chiral catalyst in condensing hydrogen cyanide and crotonaldehyde. Our work complements the large body of literature on the synthesis of 1-Deoxynojirimycin derivatives with the distinguishing feature that eight stereoisomers of this important class of glycosidase inhibitors can be derived from a common precursor in an efficient manner.

  • synthesis of l altro 1 deoxynojirimycin d allo 1 deoxynojirimycin and d galacto 1 deoxynojirimycin from a single chiral cyanohydrin
    Organic Letters, 2010
    Co-Authors: Adrianus M C H Van Den Nieuwendijk, Richard J B H N Van Den Berg, Mark Ruben, Johannes Brussee, Rene G A Boot, Gijsbert A Van Der Marel, Johannes M F G Aerts, Sander E Engelsma, Martijn D P Risseeuw, Herman S. Overkleeft

    Abstract:

    The chemoenzymatic synthesis of three 1-Deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction−transimination−sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.

Katsuhiko Matsui – 3rd expert on this subject based on the ideXlab platform

  • n containing sugars from morus alba and their glycosidase inhibitory activities
    Carbohydrate Research, 1994
    Co-Authors: Naoki Asano, Kengo Oseki, Emiko Tomioka, Haruhisa Kizu, Katsuhiko Matsui

    Abstract:

    Abstract The reexamination of N -containing sugars from the roots of Morus alba by improved purification procedures led to the isolation of eighteen N -containing sugars, including seven that were isolated from the leaves of Morus bombycis . These N -containing sugars are 1-Deoxynojirimycin ( 1 ), N -methyl-1-Deoxynojirimycin ( 2 ), fagomine ( 3 ), 3- epi -fagomine ( 4 ), 1,4-dideoxy-1,4-imino-pD-arabinitol ( 5 ), 1,4-dideoxy-1,4-imino-pD-ribitol ( 6 ), calystegin B 2 (1α,2β,3α,4β-tetrahydroxy- nor -tropane, 7 ), calystegin C 1 , (1α,2β,3α,6α-pentahydroxy- nor -tropane, 8 ), 1,4-dideoxy-1,4-imino-(2- O -β-pD-glucopyranosyl)- d -glucopyranosyl)- d -arabinitol ( 9 ), and nine glycosides of 1 . These glycosides consist of 2- O – and 6- O -α- d -galactopyranosyl-1-Deoxynojirimycins ( 10 and 11 , respectively), 2- O -, 3- O – and 4- O -α- d -glucopyranosyl-1-Deoxynojirimycins ( 12 , 13 , and 14 , respectively), and 2- O -, 3- O -, 4- O – and 6- O -β- D -glucopyranosyl-1-Deoxynojirimycins ( 15 , 16 , 17 , and 18 , respectively). Compound 4 is a new member of polyhydroxylated piperidine alkaloids, and the isolation of 6 is the first report of its natural occurrence. It has recently been found that the polyhydroxy- nor -tropane alkaloids possess potent glycosidase inhibitory activities. Calystegin A 3 is the trihydroxy- nor -tropane, and calystegins B 1 and B 2 are the tetrahydroxy- nor -tropane. Calystegin C 1 , a new member of calystegins, is the first naturally occurring pentahydroxy- nor -tropane alkaloid. The inhibitory activities of these compounds are investigated against rat digestive glycosidases and various commercially available glycosidases.

  • Enzymic synthesis of α- and β-d-glucosides of 1-Deoxynojirimycin and their glycosidase inhibitory activities
    Carbohydrate Research, 1994
    Co-Authors: Naoki Asano, Kengo Oseki, Eiichi Kaneko, Katsuhiko Matsui

    Abstract:

    Abstract 1-Deoxynojirimycin ( 1 ) is a potent inhibitor of mammalian and rice α-glucosidase. Several glucosides of 1 were synthesized by use of the native and immobilized enzyme and their effect on various enzymes was investigated. Transglucosylation reactions using rice α-glucosidase, yeast α- and β-glucosidases purified from Rhodotorula lactosa were performed with maltose or cellobiose as a glucose donor and N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 2 ) as an acceptor. The transglucosylation reaction using native rice α-glucosidase afforded 3- O -α- d -glucopyranosyl- N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 4 ), 4- O – α- d -glucopyranosyl- N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 5 ), and 2- O -α- d -gluco- pyranosyl- N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 3 ) in yields of 40, 13, and 2%, respectively, after 30 min. The transglucosylation reaction using immobilized rice α-glucosidase was similar to that using the native enzyme. In the system using native yeast α-glucosidase, 3 , 5 , and 4 were formed in yields of 34, 13, and 6%, respectively, after 15 h. The immobilization of yeast α-glucosidase caused a significant decrease in transglucosylation activity. Yeast β-glucosidase showed a high transglucosylation activity and incubation with the reaction system afforded 2- O -β- d -glucopyranosyl- N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 6 ) and 4- O -β- d -glucopyranosyl- N -(benzyloxycarbonyl)-1-Deoxynojirimycin ( 7 ) in yields of 69 and 3%, respectively, after 3 h. The transglucosylation reaction using immobilized yeast β-glucosidase preferentially afforded 6 in the yield of 73% after 3 h. After removal of N -benzyloxycarbonyl group from the product glucosides, their glycosidase inhibitory activities were measured. 3- O -α- d -Glucopyranosyl-1-Deoxynojirimycin ( 9 ) retained the potent inhibition of 1 against rat intestinal sucrase activity and was more effective than 1 against rice α-glucosidase. 4- O -α- d -Glucopyranosyl-1-Deoxynojirimycin ( 10 ) retained the potency of 1 against rat intestinal sucrase and isomaltase. 2- O -α- d -Glucopyranosyl-1-Deoxynojirimycin ( 8 ) was more effective than 1 against trehalases.