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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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A practical synthesis from siastatin B of (3S,4S,5R,6R)- 4,5-dihydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid having antimetastatic activity in mice.
T Satoh et al.
Carbohydrate research, 286, 173-178 (1996-06-05)
Y Nishimura et al.
Journal of medicinal chemistry, 40(16), 2626-2633 (1997-08-01)
L-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4- guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido) piperidine-3-carboxylic acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition
Y Nishimura et al.
The Journal of antibiotics, 47(1), 101-107 (1994-01-01)
A trifluoroacetamide analogue of siastatin B, (3S,4S,5R,6R)-6-(trifluoroacetamido)-4,5-dihydroxy-3-piperidine carboxylic acid has been chemically synthesized. This compound, as well as the previously synthesized analogue, (3R,4R,5R,6R)-6-(trifluoroacetamido)-3,4,5-trihydroxy-3-piperid inecarboxylic acid, showed marked inhibitory activity against beta-glucuronidase and significant inhibition of experimental pulmonary metastasis of the
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.
K I Kondo et al.
Natural product letters, 15(6), 371-375 (2002-02-13)
N-Alkyl-3-decarboxy-3-hydroxymethylsiastatin B, N-alkyl analogues of gem-diamine 1-N-iminosugars, is a new family of glycosidase inhibitors that have been synthesized from siastatin B isolated from Streptomyces culture. These compounds were evaluated as glycosidase inhibitors.
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