Skip to Content
Merck

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

Sign In to View Organizational & Contract Pricing.

Select a Size

All Photos(1)

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

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCX7765
MKCX0619
MKCW5200
MKCW1806
MKCT9978

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

N-glycosylation of mouse TRAIL-R restrains TRAIL-induced apoptosis
Estornes Y, et al.
Cell Death & Disease, 9(5), 494-494 (2018)
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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service