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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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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
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