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K1140

Sigma-Aldrich

Kifunensine

solid,film or powder, ≥98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H12N2O6
CAS Number:
109944-15-2
Molecular Weight:
232.19
UNSPSC Code:
12352204
NACRES:
NA.77

product name

Kifunensine, mannosidase inhibitor

biological source

synthetic (organic)

Quality Level

100

Assay

≥98%

form

film or powder
solid

solubility

water, double-distilled: 50 mM

storage temp.

−20°C

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

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)

General description

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

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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A D Elbein et al.
The Journal of biological chemistry, 265(26), 15599-15605 (1990-09-15)
Kifunensine, produced by the actinomycete Kitasatosporia kifunense 9482, is an alkaloid that corresponds to a cyclic oxamide derivative of 1-amino mannojirimycin. This compound was reported to be a weak inhibitor of jack bean alpha-mannosidase (IC50 of 1.2 x 10(-4) M)
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
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
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)
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
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