The structures of a .BETA.-galactosidase inhibitor, galactostatin, and its derivatives.

Miyake, Yukio; Ebata, Mitsuo

doi:10.1271/bbb1961.52.661

Cited by 22 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

Asymmetric synthesis of pentono‐ and 6‐deoxyhexono‐δ‐lactams via hetero‐Diels‐Alder reactions with nitroso dienophile

Defoin¹,

Sarazin²,

Sifferlen³

et al. 1998

Helvetica Chimica Acta

View full text Add to dashboard Cite

Asymmetric Didvilldrr reaction of the pentadienoic and hexadienoic acids 2a, b with the chiral chloronitroso derivative 3 gave the primary adducts 4a, b with good-to-excellent enantioselectivity. Subsequent ci.v-or rrcmv-dihydroxylation and hydrogenolytic cleavage of the N -0 bond led to the 5-amino-5-deoxypcutono-h-lactams 13a. 14, lSa, and 16 in the D-ribose, L-arabinose, 1,-xylose, and L-lyxose series, respectively, and to the 5-amino-5.6-dideoxyhexono-6-lactams 13b and 1Sh in the r,-allose and u-glucose series, respectively.Introduction. -5-Amino-5-deoxyhexono-6-lactams la are stable amino-sugars which were easily synthesized.

show abstract

mentioning

confidence: 99%

Asymmetric synthesis of pentono‐ and 6‐deoxyhexono‐δ‐lactams via hetero‐Diels‐Alder reactions with nitroso dienophile

Defoin¹,

Sarazin²,

Sifferlen³

et al. 1998

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…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%

Naturally Occurring Iminosugars and Related Alkaloids: Structure, Activity and Applications

Asano

2007

Iminosugars

View full text Add to dashboard Cite

“…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%

Recent Advances in the Total Synthesis of Piperidine Azasugars

et al. 2005

View full text Add to dashboard Cite

Since the discovery of nojirimycin, a glycosidase inhibitor, polyhydroxylated piperidines (also called azasugars: the ring O‐atom of a carbohydrate is replaced by nitrogen) have attracted considerable attention and have been the target of numerous synthetic strategies during the last decade. The efficient synthesis of naturally occurring azasugars and their analogs is of considerable importance due to their potential glycosidase inhibitor properties. Some of them have been widely investigated as candidates for drugs to treat a variety of carbohydrate‐mediated diseases such as diabetes, viral infections, including HIV, cancer metastasis, hepatitis, and Gaucher’s disease. This microreview focuses on recent syntheses of azasugars. In addition, the biology of these compounds is briefly considered. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

show abstract

The structures of a .BETA.-galactosidase inhibitor, galactostatin, and its derivatives.

Cited by 22 publications

References 0 publications

Asymmetric synthesis of pentono‐ and 6‐deoxyhexono‐δ‐lactams via hetero‐Diels‐Alder reactions with nitroso dienophile

Asymmetric synthesis of pentono‐ and 6‐deoxyhexono‐δ‐lactams via hetero‐Diels‐Alder reactions with nitroso dienophile

Naturally Occurring Iminosugars and Related Alkaloids: Structure, Activity and Applications

Recent Advances in the Total Synthesis of Piperidine Azasugars

Contact Info

Product

Resources

About