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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
Pricing and availability is not currently available.

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

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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)
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
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.
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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