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Merck
CN

K1140

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

Key Documents

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Product Name

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)

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

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX7765
MKCX0619
MKCW5200
MKCW1806
MKCT9978

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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)
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)
N-glycosylation of mouse TRAIL-R restrains TRAIL-induced apoptosis
Estornes Y, et al.
Cell Death & Disease, 9(5), 494-494 (2018)
Kirk W Hering et al.
The Journal of organic chemistry, 70(24), 9892-9904 (2005-11-19)
[reaction: see text] A practical synthesis of the potent class I alpha-mannosidase inhibitor kifunensine (1) beginning from the inexpensive and readily available starting material L-ascorbic acid (15) is described. The protected amino-alcohol ((2R,3R,4R,5R)-5-amino-2,3:4,6-diisopropylidenedioxyhexanol, 11) served as a key intermediate from
Andrew I Flyak et al.
Cell host & microbe, 24(5), 703-716 (2018-11-16)
Hepatitis C virus (HCV) vaccine efforts are hampered by the extensive genetic diversity of HCV envelope glycoproteins E1 and E2. Structures of broadly neutralizing antibodies (bNAbs) (e.g., HEPC3, HEPC74) isolated from individuals who spontaneously cleared HCV infection facilitate immunogen design to elicit antibodies against multiple
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