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Merck
CN

K1140

Kifunensine

solid,film or powder, ≥98%

别名:

FR 900494, 六氢6R，7S，8aS-三羟基-5R-（羟甲基）-咪唑并[1,2-a]吡啶-2,3-二酮

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关于此项目

经验公式（希尔记法）:
C8H12N2O6
化学文摘社编号:
109944-15-2
分子量:
232.19
UNSPSC Code:
12352204
NACRES:
NA.77

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产品名称

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已用作Jurkat T细胞、人胚胎肾脏（HEK293T / 17）细胞和小鼠胚胎成纤维细胞中的甘露糖苷酶I抑制剂。

Biochem/physiol Actions

Kifunensine是一类糖蛋白加工甘露糖苷酶的选择性抑制剂。
Kifunensine通过抑制内质网相关的甘露糖苷酶的活性来抑制内质网相关的降解(ERAD)。它也是I类CAZy糖基水解酶家族47的糖苷酶抑制剂。

General description

Kifunensine是一种生物碱化合物，从放线菌Kitasporia kifunensis中分离出来。

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

涉药品监管产品
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历史批次信息供参考:

分析证书(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-glycan content modulates kainate receptor functional properties
Vernon CG, et al.
The Journal of Physiology, 595(17), 5913-5930 (2017)
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
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
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)
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