Kifunensine

Names

[ Name ]:
Kifunensine

[Synonym ]:
(5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione
Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-
KIFUNENSINE,KITASATOSPORIA KIFUNENSE
1-deoxymannojirimycin
Kifunensine

Biological Activity

[Description]:

Kifunensine, a potent and selective inhibitor of class I α-mannosidases isolated from Actinomycete, prevents α-mannosidases I from trimming mannose residues on glycoproteins. Kifunensine inhibits ERAD[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Kifunensine, an alkaloid from actinomycete Kitasatosporia kifunense 9482, is the most efficient nhibitor of a-mannosidase I, blocking N-glycan synthesis at an8GlcNAc2 (Man8) or Man9GlcNAc2 (Man9) stage[3]. RT-PCR[3]. Cell Line: Hybridoma cells expressing a human IgG1 monoclonal Antibody[3]. Concentration: 2 μg/mL. Incubation Time: 4 days. Result: Significantly reduced the lentil lectin binding. Kifunensine is the most effective among the inhibitors tested in producing antibodies containing oligomannose residues without fucose.

[In Vivo]

Animal Model: BALB/c mice[3]. Dosage: 5 mg/kg. Administration: IV via tail vein. Result: There was no significant difference in the serum levels of anti-TEM B mAb generated from cells treated with or without kifunensine in the 7-day period.

[References]

[1]. Yongao Xiong, et al. Glycoform Modification of Secreted Recombinant Glycoproteins through Kifunensine Addition during Transient Vacuum Agroinfiltration. Int J Mol Sci. 2018 Mar; 19(3): 890.

[2]. Hiroshi Kayakiri, et al. Structure of Kifunensine, a New Immunomodulator Isolated from an Actinomycete. J. Org. Chem. 1989,54,4015-4016.

[3]. Qun Zhou, et al. Development of a Simple and Rapid Method for Producing Non-Fucosylated Oligomannose Containing Antibodies With Increased Effector Function. Biotechnol Bioeng. 2008 Feb 15;99(3):652-65.

[4]. Hyung Lim Elfrink, et al. Inhibition of Endoplasmic Reticulum Associated Degradation Reduces Endoplasmic Reticulum Stress and Alters Lysosomal Morphology and Distribution. Mol Cells. 2013 Apr 30; 35(4): 291–297.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Melting Point ]:
>280â„ƒ

[ Molecular Formula ]:
C₈H₁₂N₂O₆

[ Molecular Weight ]:
232.191

[ Exact Mass ]:
232.069534

[ PSA ]:
130.33000

[ LogP ]:
-2.21

[ Index of Refraction ]:
1.706

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

A context-independent N-glycan signal targets the misfolded extracellular domain of Arabidopsis STRUBBELIG to endoplasmic-reticulum-associated degradation.

Biochem. J. 464(3) , 401-11, (2014)

N-glycosylation of proteins plays an important role in the determination of the fate of newly synthesized glycoproteins in the endoplasmic reticulum (ER). Specific oligosaccharide structures recruit m...

Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase.

Carbohydr. Res. 365 , 1-8, (2013)

An efficient and practical synthesis of kifunensine thioanalogs 1a-c was reported. The bicyclic azasugars fused thiazolidin-4-one 4a-c as key intermediates were first synthesized in good yields of 74-...

Evolution of cross-neutralizing antibody specificities to the CD4-BS and the carbohydrate cloak of the HIV Env in an HIV-1-infected subject.

PLoS ONE 7(11) , e49610, (2012)

Broadly neutralizing antibodies are considered an important part of a successful HIV vaccine. A better understanding of the factors underlying their development during infection and of the epitopes th...

Related Compounds

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