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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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0375
MKCP9287
MKCG6277
MKCF5585
MKCD2855

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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
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)
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.
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.
Bioorganic & medicinal chemistry, 4(1), 91-96 (1996-01-01)
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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