Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus

Hardick, David J.; Hutchinson, D. W.; Trew, Sally J.; Wellington, E. M. H.

doi:10.1016/s0040-4020(01)88220-x

Cited by 75 publications

(37 citation statements)

References 18 publications

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“…2 (Hardick et al, 1992). From this finding, it could be considered that some pentoses may be precursors of nectrisine (1), as it contains five carbon atoms.…”

Section: Screening Of Factors Affecting the Production Of Nectrisine (1)mentioning

confidence: 98%

Biosynthesis of nectrisine in Thelonectria discophora SANK 18292

et al. 2015

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“…2 (Hardick et al, 1992). From this finding, it could be considered that some pentoses may be precursors of nectrisine (1), as it contains five carbon atoms.…”

Section: Screening Of Factors Affecting the Production Of Nectrisine (1)mentioning

confidence: 98%

Biosynthesis of nectrisine in Thelonectria discophora SANK 18292

et al. 2015

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“…These results supported the previous studies reporting that DMJ present in Streptomyces species was absent in Bacillus species which was proved through isotope labeling studies. 8,11) DMJ production was confirmed only in recombinant Escherichia coli harboring the DNJ biosynthetic gene cluster isolated from Bacillus species, and not in the wild type.…”

Section: )mentioning

confidence: 96%

Isolation of the Putative Biosynthetic Gene Cluster of 1-Deoxynojirimycin by <i>Bacillus amyloliquefaciens</i> 140N, Its Production and Application to the Fermentation of Soybean Paste

Seo

Nam

Lee

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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“…It was also discovered in the culture broths of various species of Streptomyces lavendulae (MATSUMURA et al 1979c;MlTsuo and SAWAO 1980;MURAO and MIYATA 1980;EZURE et al 1985) and S. subrutilus (HARDICK et al 1991(HARDICK et al ,1992. Compared with nojirimycin, 1-deoxynojirimycin is a weaker inhibitor of nonmammalian and mammalian ß-glucosidases (NIWA et al 1970;see also: TRUSCHEIT et al 1981;MÜLLER 1985;SCOFIELD et al 1986;TRUSCHEIT 1987;ELBEIN 1987;TRUSCHEIT et al 1988;YOSHIKUNI et al 1988;LEGLER 1990;NISHIMURA 1991;YOSHIKUNI 1991;ROBINSON et al 1992;HUGHES and RUDGE 1994).…”

Section: I-deoxynojirimycinmentioning

confidence: 98%

Chemistry and Structure-Activity Relationships of Glucosidase Inhibitors

Junge¹,

Matzke²,

Stoltefuß³

1996

Oral Antidiabetics

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A. IntroductionWhen intestinal sucrase and pancreatic a-amylase were identified at Bayer as new targets for improved diabetes therapy (PULS et al. 1973), the problem remained of the best way to find a potent and selective inhibitor of these enzymes. The medicinal chemist today has two alternatives in the search for a first lead compound, firstly the screening of thousands of compounds with maximum structural diversity in a random screening approach, or secondly the rational design of a lead compound, when the biochemical mechanism and the structure of the enzyme are weIl known. In the late 1960s, when we started to look for such potent and selective inhibitors, we had to choose the random screening approach, relying mainly on testing of extracts of the culture broths of microorganisms.Today the mechanism of enzymatic splitting of sucrose by intestinal sucrase is fairly weIl understood. First the glucosidic oxygen atom of sucrose is protonated via a carboxyl group of the enzyme. The splitting of the glucosidic C-O bond is further facilitated by the glucosyl cation being stabilized by a second carboxylate group of the enzyme (COGOLI and SEMENZA 1975). FinaIly, the glucosyl cation reacts with water to give the products 0-glucose and o-fructose. The protonated sucrose molecule land the glucosyl cation 11 are two high-energy intermediates of the enzymatic reaction. Today we know that mimics of such high-energy intermediates are often potent inhibitors of the enzyme. Accordingly, compounds similar in structure to o-glucose but with an easily protonated basic N-atom either in the position of the anomeric oxygen atom (inhibitor type I) or in the position of the ring oxygen atom (inhibitor type 11) should be potent inhibitors of sucrase (Fig. 1). Interestingly, both types of inhibitors represented by either acarbose or I-deoxynojirimycin were found in our random screening. In the foIlowing sections these two types of inhibitors are not discussed in a historical order but under structural criteria. Not included in this discussion are the a-amylase inhibitors of protein nature because there is no evidence that they will find any therapeutic application.

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Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus

Cited by 75 publications

References 18 publications

Biosynthesis of nectrisine in Thelonectria discophora SANK 18292

Biosynthesis of nectrisine in Thelonectria discophora SANK 18292

Isolation of the Putative Biosynthetic Gene Cluster of 1-Deoxynojirimycin by <i>Bacillus amyloliquefaciens</i> 140N, Its Production and Application to the Fermentation of Soybean Paste

Chemistry and Structure-Activity Relationships of Glucosidase Inhibitors

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