Siastatin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03512 |
| CAS | 54795-58-3 |
| Molecular Weight | 218.21 |
| Molecular Formula | C8H14N2O5 |
| Purity | 95% |
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Description
A-72363 B is a Heparanase inhibitor produced by Streptomyces nobilis SANK 60192.
Specification
| Synonyms | A-72363 B; 3-Piperidinecarboxylic acid, 6-(acetylamino)-4,5-dihydroxy-, (3S-(3-alpha,4-alpha,5-alpha,6-beta))-; Siastatin B microbial; (2s,3r,4s,5s)-2-(Acetylamino)-5-Carboxy-3,4-Dihydroxypiperidinium |
| Storage | -20°C |
| IUPAC Name | (3S,4S,5R,6R)-6-acetamido-4,5-dihydroxypiperidine-3-carboxylic acid |
| Canonical SMILES | CC(=O)NC1C(C(C(CN1)C(=O)O)O)O |
| InChI | InChI=1S/C8H14N2O5/c1-3(11)10-7-6(13)5(12)4(2-9-7)8(14)15/h4-7,9,12-13H,2H2,1H3,(H,10,11)(H,14,15)/t4-,5-,6-,7+/m0/s1 |
| InChI Key | DQTKLICLJUKNCG-ZTYPAOSTSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 579.2±50.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1.Synthesis of the sialidase inhibitor siastatin B.
Knapp S1, Zhao D. Org Lett. 2000 Dec 14;2(25):4037-40.
[structure] The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta-lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.
2.Synthesis and activity of 1-N-iminosugar inhibitors, siastatin B analogues for alpha-N-acetylgalactosaminidase and beta-N-acetylglucosaminidase.
Nishimura Y1, Satoh T, Kudo T, Kondo S, Takeuchi T. Bioorg Med Chem. 1996 Jan;4(1):91-6.
N-Acetylgalactosamine-based 1-N-iminosugars, new types of glycosidase inhibitor have been synthesized by modeling on siastatin B, isolated from a Streptomyces culture. The analogues of siastatin B were proved to be potent inhibitors for alpha-N-acetylgalactosaminidase and/or beta-N-acetylglucosaminidase.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
