79831-76-8 Usage
Description
Castanospermine is a plant alkaloid that acts as a potent inhibitor of both αand β-glucosidases, including lysosomal and neutral α-glucosidases, as well as lysosomal and cytosolic β-glucosidases. It effectively blocks N-linked glycosylation during post-translational modification of proteins, impacting protein trafficking and cell functions that rely on glycosylation, such as angiogenesis. Additionally, castanospermine interferes with viral replication and infection dependent on glucosidase activity.
Uses
Used in Pharmaceutical Industry:
Castanospermine is used as a glycosidase inhibitor and anti-inflammatory agent for its ability to inhibit syncytium formation between HIV-infected and CD4-expressing cells, potentially interfering with infectivity. It also demonstrates inhibitory effects on inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis.
Used in Enzyme Inhibition:
Castanospermine is used as an inhibitor of Glucosidase I, Maltase-glucoamylase, and MANBA, effectively blocking the activity of these enzymes and their role in glycoprotein processing.
Used in Virology Research:
As a potent inhibitor of αand β-glucosidases, especially glucosidase I, which is required for glycoprotein processing by transfer of mannose and glucose from asparagine-linked lipids, castanospermine is utilized in research to study the effects of inhibiting HIV syncytium formation and replication.
Used in Biochemistry:
Castanospermine is used as an α-L-fucosidases inhibitor, playing a role in the study and regulation of enzyme activity related to the fucosylation process in glycoconjugates and glycoproteins.
Biological Activity
Potent inhibitor of α - and β -glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids). Inhibits HIV syncytium formation and replication.
References
1) Saul et al. (1984), Studies on the mechanism of castanospermine inhibition of alpha- and beta-glucosidases; Arch. Biochem. Biophys, 230 668
2) Repp et al. (1985), The effects of processing inhibitors on N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles; J. Biol. Chem., 260 15873
3) Gruters et al. (1987), Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase; Nature, 330 74
4) Franc et al. (1990), Effects of deoxymannojirimycin and castanospermine on the polarized secretion of thyroglobulin; Endocrinology, 126 1464
5) Pili et al. (1995), The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth; Mol. Cancer Res., 55 2920
6) Rhinehart et al. (1987), Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: a result of intestinal disaccharidase inhibition; Life Sci., 41 2325
Check Digit Verification of cas no
The CAS Registry Mumber 79831-76-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,8,3 and 1 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 79831-76:
(7*7)+(6*9)+(5*8)+(4*3)+(3*1)+(2*7)+(1*6)=178
178 % 10 = 8
So 79831-76-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5?,6+,7+,8?/m0/s1
79831-76-8Relevant articles and documents
An efficient, highly stereoselective synthesis of (+)-castanospermine
Anzeveno, Peter B.,Angell, Paul T.,Creemer, Laura J.,Whalon, Michael R.
, p. 4321 - 4324 (1990)
An efficient, highly stereoselective synthesis of (+)-castanospermine (1) has been achieved from 1,2-0-isopropylidene-α-Dglucofuranurono-6,3-lactone (2).
Stereoselective Total Syntheses of (+)-Castanospermine and Neu5Ac Methyl Ester
Myeong, In-Soo,Lee, Yong-Taek,Kang, Jihun,Ham, Won-Hun
, p. 4211 - 4220 (2019/04/30)
Concise and stereocontrolled total syntheses of (+)-castanospermine and N-acetylneuraminic acid methyl ester were achieved from diastereomerically enriched anti,syn,syn-1,3-oxazine and anti,syn,anti-1,3-oxazine, respectively. The key step in this strategy was the stereoselective BF3·OEt2-mediated allylation.
A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi- castanospermine
Liu, Gang,Wu, Tian-Jun,Ruan, Yuan-Ping,Huang, Pei-Qiang
experimental part, p. 5755 - 5768 (2010/08/19)
The asymmetric total synthesis of natural azasugars (+)-castanospermine, (+)-7-deoxy-6-epI-castanospermine, and synthetic (+)-1-epi-castanospermine has been accomplished in nine to ten steps from a common chiral building block (S)-8. The method features a powerful chiral relay strategy consisting of a highly diastereoselective vinylogous Mukaiyama-type reaction with either chiral or achiral aldehydes (≥ 95% de; de = diastereomeric excess) and a diastereodivergent reduction of tetramic acids, which allows formation of three continuous stereogenic centers with high diastereo-selectivities. The method also provides a flexible access to structural arrays of 5-(α-hydroxyalkyl) tetramic acids, such as 17/34, and 5-(α-hydroxyalkyl)-4-hydroxyl-2- pyrrolidinones, such as 18 and 25/35 a. The method constitutes the first realization of the challenging chiral synthons A and D and thus of the conceptually attractive retrosynthetic analysis shown in Scheme 1 in a highly enantioselective manner.
Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation
Ceccon, Julien,Danoun, Gregory,Greene, Andrew E.,Poisson, Jean-Franois
scheme or table, p. 2029 - 2031 (2009/09/04)
An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.
