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S8063

Sigma-Aldrich

Siastatin B

lyophilized powder, from microbial

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

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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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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