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Merck
CN

S8063

Sigma-Aldrich

Siastatin B

lyophilized powder, from microbial

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别名:
(3S, 4S, 5R, 6R)-6-(Acetylamino)-4,5-dihydroxy-3-piperidinecarboxylic acid
经验公式(希尔记法):
C8H14N2O5
CAS号:
分子量:
218.21
MDL编号:
UNSPSC代码:
12352202
PubChem化学物质编号:
NACRES:
NA.77

生物来源

microbial

质量水平

形式

lyophilized powder

包装

vial of 23.0 μmol

溶解性

H2O: 2.3 mL/vial (for a 10 mM solution)

储存温度

−20°C

SMILES字符串

CC(=O)N[C@H]1NC[C@@H]([C@H](O)[C@@H]1O)C(O)=O

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

应用

Broad spectrum inhibitor of sialidase.

生化/生理作用

Streptomyces metabolite, a broad-spectrum inhibitor of neuraminidase (sialidase).

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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S Knapp et al.
Organic letters, 2(25), 4037-4040 (2000-12-12)
[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.
Y Kawase et al.
The Journal of antibiotics, 49(1), 61-64 (1996-01-01)
Inhibitory activities of A-72363 A-1, A-2 and C, the diastereomers of a neuraminidase inhibitor siastatin B, against various glycosidases were tested in comparison to siastatin B. Despite these compounds differing only in their configuration, each compound showed strikingly different specificities
E Shitara et al.
Organic letters, 2(24), 3837-3840 (2000-12-02)
[reaction: see text] 6-Acetamido-5-amino- and -5-guanidino-3, 4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 and 9) have been synthesized starting from natural siastatin B, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors
Y Nishimura et al.
The Journal of antibiotics, 45(6), 963-970 (1992-06-01)
Siastatin B analogues, optically active 2-(trifluoroacetamide)- 3,4,5-trihydroxypiperidines having nitromethyl, aminomethyl and carboxyl branched groups at C-5, and (+)-(2R,3R,4R,5R)-5-(aminomethyl)-3,4,5-trihydroxy-2- (hydroxyacetamido)piperidine have been obtained total synthetically from D-ribono-1,4-lactone. Some analogues have inhibitory activity against some glycosidases, and (+)-(2R,3R,4R,5R)-2-(trifluoroacetamido)-3,4,5-trihydroxypiperi dine-5-carboxylic acid showed a
T Kudo et al.
The Journal of antibiotics, 45(10), 1662-1668 (1992-10-01)
N-Substituted derivatives of siastatin B have been obtained by a chemical modification. Some derivatives showed potent inhibitory activities against Streptococcus sp. and Clostridium perfringens neuraminidases.

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