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S8063

Sigma-Aldrich

Siastatin B

lyophilized powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C8H14N2O5
CAS-Nummer:
54795-58-3
Molekulargewicht:
218.21
MDL-Nummer:
MFCD01631253
UNSPSC-Code:
12352202
PubChem Substanz-ID:
24899775
NACRES:
NA.77

product name

Siastatin B, lyophilized powder, from microbial

Biologische Quelle

microbial

Qualitätsniveau

100

Form

lyophilized powder

Verpackung

vial of 23.0 μmol

Löslichkeit

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

Lagertemp.

−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

InChIKey

DQTKLICLJUKNCG-ZTYPAOSTSA-N

Anwendung

Broad spectrum inhibitor of sialidase.

Biochem./physiol. Wirkung

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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T Takatsu et al.
The Journal of antibiotics, 49(1), 54-60 (1996-01-01)
Novel heparanse inhibitors, A72363 A-1, A-2, and C, were isolated from the culture filtrate of Streptomyces nobilis SANK 60192 by column chromatography on various resinous adsorbents, followed by preparative anion exchange HPLC. Spectroscopic studies revealed that they are diastereomers of
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.
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.
Synthesis and antimetastatic activity of 6-trichloroacetamido and 6-guanidino analogues of siastatin B.
T Satoh et al.
The Journal of antibiotics, 49(3), 321-325 (1996-03-01)
T Kudo et al.
The Journal of antibiotics, 45(6), 954-962 (1992-06-01)
Totally synthetic analogues of siastatin B, optically active 2-acetamido-3,4,5-trihydroxypiperidines having the nitromethyl, aminomethyl and carboxyl branched groups at C-5 have been obtained from D-ribono-1,4-lactone by a stereospecific convergent method. Some analogues showed inhibitory activity against some glycosidases.
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