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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)

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

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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Yusuke Saijo et al.
The EMBO journal, 28(21), 3439-3449 (2009-09-19)
Pattern recognition receptors in eukaryotes initiate defence responses on detection of microbe-associated molecular patterns shared by many microbe species. The Leu-rich repeat receptor-like kinases FLS2 and EFR recognize the bacterial epitopes flg22 and elf18, derived from flagellin and elongation factor-Tu
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
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
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
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