An inhibitor of glycoprotein biosynthesis
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Kifunensine

Item No. 10009437

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione
CAS Number
109944-15-2
Synonyms
  • FR900494
Molecular Formula
C8H12N2O6
Formula Weight
232.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Warm Distilled Water: 0.5 mg/ml
λmax
225 nm
SMILES
O[C@H]1[C@H](O)[C@H](O)[C@](NC(C2=O)=O)([H])N2[C@@H]1CO
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $74

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    5 mg

    $203

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    10 mg

    $295

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    50 mg

    $1,106

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    Product Description

    Kifunensine was originally isolated from the actinomycete Kitasatosporia kifunensine No. 9482 and shown to be a weak inhibitor of aryl mannosidase.1,2 It has since been shown to be a potent and selective inhibitor of class I α-mannosidases and may serve as a key inhibitor of glycoprotein biosynthesis.3 Kifunensine inhibits both human endoplasmic reticulum α-1,2-mannosidase I and members of the Golgi subfamily of the class I mannosidases (Golgi α-mannosidase IA, IB, and IC) exhibiting Ki values of 130 and 23 nM, respectively. It also inhibits mung bean α-1,2-mannosidase I with an IC50 value of 20-50 nM.3 Kifunensine can be used to block α-mannosidase I activity at the endoplasmic reticulum (ER), preventing the removal of desired mutated proteins through ER quality control mechanisms.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwami, M., Nakayama, O., Terano, H., et al. A new immunomodulator, FR-900494: Taxonomy, fermentation, isolation, and physico-chemical and biological characteristics. J. Antibiot. (Tokyo) XL(5), 612-622 (1987).

    2. Kayakiri, H., Takase, S., Shibata, T., et al. Structure of kifunensine, a new immunomodulator isolated from an actinomycete. The Journal of Organic Chemistry 54, 4015-4016 (1989).

    3. Hering, K.W., Karaveg, K., Moremen, K.W., et al. A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum α-mannosidase I. The Journal of Organic Chemistry 70, 9892-9904 (2005).

    4. Bartoli, M., Gicquel, E., Barrault, L., et al. Mannosidase I inhibition rescues the human α-sarcoglycan R77C recurrent mutation. Hum. Mol. Genet. 17(9), 1214-1221 (2008).

    5. Soheili, T., Gicquel, E., Poupiot, J., et al. Rescue of sarcoglycan mutations by inhibition of endoplasmic reticulum quality control is associated with minimal structural modifications. Hum. Mutat. 33(2), 429-439 (2012).