K1140

Kifunensine

Name: Kifunensine
Brand: SIGMA

solid,film or powder, ≥98%

Sinónimos:

FR 900494, Hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a] pyridine-2,3-dione

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About This Item

Fórmula empírica (notación de Hill):

C₈H₁₂N₂O₆

Número CAS:

109944-15-2

Peso molecular:

232.19

UNSPSC Code:

12352204

NACRES:

NA.77

Nombre del producto

Kifunensine, mannosidase inhibitor

SMILES string

N21[C@H](NC(=O)C2=O)[C@H]([C@H]([C@@H]([C@H]1CO)O)O)O

InChI

1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1

InChI key

OIURYJWYVIAOCW-PQMKYFCFSA-N

biological source

synthetic (organic)

assay

≥98%

form

film or powder
solid

solubility

water, double-distilled: 50 mM

storage temp.

−20°C

Quality Level

100

Gene Information

human ... MAN1A1(4121), MAN1A2(10905), MAN1B1(11253), MAN1C1(57134)
mouse ... MAN1A1(17155), MAN1A2(17156), MAN1B1(227619), MAN1C1(230815)
rat ... MAN1A1(294410), MAN1A2(295319), MAN1B1(499751), MAN1C1(362625)

Application

Kifunensine has been used as an inhibitor of mannosidase I in Jurkat T-cells, human embryonic kidney (HEK293T/17) cells and in mouse embryonic fibroblast cells.

Biochem/physiol Actions

Kifunensine is a selective inhibitor of class I glycoprotein-processing α-mannosidases.

Kifunensine suppresses endoplasmic reticulum-associated degradation (ERAD) via the inhibition of endoplasmic reticulum-associated mannosidase activity. It is also a glycosidase inhibitor for Class I CAZy glycosylhydrolase family 47.

General description

Kifunensine is an alkaloid compound, isolated from the actinomycete Kitasporia kifunensis.

pictograms

GHS07

signalword

Warning

hcodes

H319

pcodes

P264 - P280 - P305 + P351 + P338 - P337 + P313

Hazard Classifications

Eye Irrit. 2

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

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N-glycosylation of asparagine 8 regulates surface expression of major histocompatibility complex class I chain-related protein A (MICA) alleles dependent on threonine 24

Mellergaard M, et al.

The Journal of Biological Chemistry, 289(29), 20078-20091 (2014)

Role of the endoplasmic reticulum-associated degradation (ERAD) pathway in degradation of hepatitis C virus envelope proteins and production of virus particles.

Mohsan Saeed et al.

The Journal of biological chemistry, 286(43), 37264-37273 (2011-09-01)

Viral infections frequently cause endoplasmic reticulum (ER) stress in host cells leading to stimulation of the ER-associated degradation (ERAD) pathway, which subsequently targets unassembled glycoproteins for ubiquitylation and proteasomal degradation. However, the role of the ERAD pathway in the viral

An ultralong CDRH2 in HCV neutralizing antibody demonstrates structural plasticity of antibodies against E2 glycoprotein.

Andrew I Flyak et al.

eLife, 9 (2020-03-04)

A vaccine protective against diverse HCV variants is needed to control the HCV epidemic. Structures of E2 complexes with front layer-specific broadly neutralizing antibodies (bNAbs) isolated from HCV-infected individuals, revealed a disulfide bond-containing CDRH3 that adopts straight (individuals who clear

Inhibition of mammalian glycan biosynthesis produces non-self antigens for a broadly neutralising, HIV-1 specific antibody.

Christopher N Scanlan et al.

Journal of molecular biology, 372(1), 16-22 (2007-07-17)

The HIV envelope has evolved a dense array of immunologically "self" carbohydrates that efficiently protect the virus from antibody recognition. Nonetheless, one broadly neutralising antibody, IgG1 2G12, has been shown to recognise a cluster of oligomannose glycans on the HIV-1

Development of a simple and rapid method for producing non-fucosylated oligomannose containing antibodies with increased effector function.

Qun Zhou et al.

Biotechnology and bioengineering, 99(3), 652-665 (2007-08-08)

Glycosylation in the Fc region of antibodies has been shown to play an important role in antibody function. In the current study, glycosylation of human monoclonal antibodies was metabolically modulated using a potent alpha-mannosidase I inhibitor, kifunensine, resulting in the

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