S8195
Swainsonine
from Metarrhizium anisopliae, ≥98% (TLC)
Synonym(s):
(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
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About This Item
Empirical Formula (Hill Notation):
C8H15NO3
CAS Number:
Molecular Weight:
173.21
Beilstein:
4175740
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85
biological source
Metarrhizium anisopliae
Quality Level
Assay
≥98% (TLC)
form
lyophilized powder
storage condition
(Keep container tightly closed in a dry and well-ventilated place.)
color
white to faint yellow
solubility
H2O: soluble 1 mg/mL
antibiotic activity spectrum
neoplastics
Mode of action
enzyme | inhibits
storage temp.
2-8°C
SMILES string
O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)C12
InChI
1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7?,8-/m1/s1
InChI key
FXUAIOOAOAVCGD-DCDLSZRSSA-N
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Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II. It inhibits glycoprotein processing and also acts as immune modulator.
Swainsonine is an indolizidine alkaloid from the plant Metarrhizium anisopliae that is used as a potent α-mannosidase inhibitor. Product S8195 has been used in chemical inhibition assays of CHO Lec2 cells to inhibit glycosylation .
Biochem/physiol Actions
Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity . It also inhibits glycoprotein processing.
Packaging
1MG
Preparation Note
Soluble in water, methanol, DMSO
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Shen Shen et al.
The Journal of biological chemistry, 286(15), 13532-13540 (2011-02-19)
Sialylated glycans serve as cell surface attachment factors for a broad range of pathogens. We report an atypical example, where desialylation increases cell surface binding and infectivity of adeno-associated virus (AAV) serotype 9, a human parvovirus isolate. Enzymatic removal of
Daniel Cook et al.
Journal of chemical ecology, 38(2), 195-203 (2012-01-28)
Locoweeds are defined as Astragalus and Oxytropis species that cause intoxication due to the alkaloid swainsonine. Swainsonine concentrations in Oxytropis sericea were influenced by location, plant part, and the developmental stage of the plant. Concentrations followed similar trends at each
Zhaocai Li et al.
International journal of biological sciences, 8(3), 394-405 (2012-03-07)
Swainsonine (1, 2, 8-trihyroxyindolizidine, SW), a natural alkaloid, has been reported to exhibit anti-cancer activity on several mouse models of human cancer and human cancers in vivo. However, the mechanisms of SW-mediated tumor regression are not clear. In this study
Glenn Archibald et al.
The Journal of organic chemistry, 77(18), 7968-7980 (2012-08-16)
Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine
Vijay Dhand et al.
Organic letters, 15(8), 1914-1917 (2013-04-05)
A short synthesis of hydroxyalkyl dihydropyrroles has been developed that involves the coupling of propargylamines with α-chloroaldehydes, followed by Lindlar reduction and a one-pot epoxide formation/opening sequence. The application of this process to the synthesis of unnatural iminosugars and a
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