1988
DOI: 10.1271/bbb1961.52.661
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The structures of a .BETA.-galactosidase inhibitor, galactostatin, and its derivatives.

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Cited by 22 publications
(10 citation statements)
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“…The conformation of the lactams seems also to be determined by the H-bond between OH-C(2) and the C(1)-carbonyl group which fixes this OH group in itsequatorial position, as also (for 13b and 15b) by the equatorial C(5) substituent. Both these effects determine also the same half-chair conformation of S-lactams in the D-glUCOniC [6] [47] and D-galactonic [48] series, and can explain the unexpected twist-boat conformation which was observed for the D-mannono-&lactam [3].…”
mentioning
confidence: 99%
“…The conformation of the lactams seems also to be determined by the H-bond between OH-C(2) and the C(1)-carbonyl group which fixes this OH group in itsequatorial position, as also (for 13b and 15b) by the equatorial C(5) substituent. Both these effects determine also the same half-chair conformation of S-lactams in the D-glUCOniC [6] [47] and D-galactonic [48] series, and can explain the unexpected twist-boat conformation which was observed for the D-mannono-&lactam [3].…”
mentioning
confidence: 99%
“…In 1988, galactostatin (galactonojirimycin) (36) was isolated from the fermentation broth of Streptomyces lydicus PA-5726 [83]. Galactostatin as well as NJ (1) can be converted to 1-deoxygalactonojirimycin (DGJ) (37) by catalytic hydrogenation with platinum catalyst or chemical reduction with NaBH 4 [83].…”
Section: -And -Galactosidase Inhibitors 241 Structures and In Vitromentioning
confidence: 99%
“…Galactostatin as well as NJ (1) can be converted to 1-deoxygalactonojirimycin (DGJ) (37) by catalytic hydrogenation with platinum catalyst or chemical reduction with NaBH 4 [83]. Galactostatin is known to be a powerful inhibitor of bacterial and fungal -galactosidases and also to be an extremely potent inhibitor of plant and bacterial -galactosidases, with K i values ranging from 100-0.7 nM [84,85].…”
Section: -And -Galactosidase Inhibitors 241 Structures and In Vitromentioning
confidence: 99%
“…Olefin 196 was also considered as an intermediate for the synthesis of DMJ (10). Cleavage of the PMB group of 196 under acidic conditions proceeded smoothly and the corresponding allylic alcohol was subjected to standard Mitsunobu inversion to give the benzoate 200 (68 % yield).…”
Section: Sharpless Asymmetric Oxidationsmentioning
confidence: 99%