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S8063

Sigma-Aldrich

Siastatin B

lyophilized powder

Synonym(s):

(3S, 4S, 5R, 6R)-6-(Acetylamino)-4,5-dihydroxy-3-piperidinecarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C8H14N2O5
CAS Number:
54795-58-3
Molecular Weight:
218.21
MDL number:
MFCD01631253
UNSPSC Code:
12352202
PubChem Substance ID:
24899775
NACRES:
NA.77

product name

Siastatin B, lyophilized powder, from microbial

biological source

microbial

Quality Level

100

form

lyophilized powder

packaging

vial of 23.0 μmol

solubility

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

storage temp.

−20°C

SMILES string

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

Application

Broad spectrum inhibitor of sialidase.

Biochem/physiol Actions

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Syntheses of the potent inhibitors of neuraminidase, N-(1,2-dihydroxypropyl) derivatives of siastatin B and its 4-deoxy analogs.
T Kudo et al.
The Journal of antibiotics, 46(2), 300-309 (1993-02-01)
E Shitara et al.
Bioorganic & medicinal chemistry, 7(6), 1241-1246 (1999-07-31)
gem-Diamine 1-N iminosugars of D-glucose-type, a new type of glycosidase inhibitors, have been synthesized from siastatin B, isolated from Streptomyces culture. 2-Trifluoroacetamido-1-N-iminosugar, (2S,3R,4R,5R)-2-trifluoroacetamido-5-hydroxymethylpiperidine -3,4-diol was proved to be a potent inhibitor for alpha-D- and beta-D-glucosidases (IC50 1.9x10(-7) and 4.2x10(-7) M
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.
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
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