109944-15-2 Usage
Uses
1. Used in Pharmaceutical Industry:
Kifunensine is used as an inhibitor of mannosidase I for its potential therapeutic applications in various diseases. Its inhibition of glycoprotein processing can be beneficial in the treatment of conditions related to the misfolding of proteins.
2. Used in Research and Development:
Kifunensine is used as a research tool for studying the role of mannosidase I in cellular processes and its potential as a target for therapeutic intervention.
3. Used in Drug Design and Development:
Kifunensine's potent inhibition of mannosidase I makes it a valuable compound in the design and development of new drugs targeting this enzyme for various therapeutic applications.
4. Used in the Treatment of Limb Girdle Muscular Dystrophy Type 2D:
Kifunensine is used as a pharmacological approach for patients carrying mutations that impair α-sarcoglycan trafficking, as its inhibition of endoplasmic reticulum α-mannosidase I activity can rescue the human α-sarcoglycan R77C mutation.
5. Used in Improving Maturation of Misfolded Proteins:
Kifunensine is used to enhance the maturation of misfolded proteins, which can be beneficial in the treatment of diseases caused by protein misfolding.
Biological Activity
Inhibitor of class I α -mannosidases that inhibits glycoprotein processing. Inhibits human endoplasmic reticulum α -1,2-mannosidase I and Golgi Class I mannosidases IA, IB and IC with K i values of 130 and 23 nM respectively.
Biochem/physiol Actions
Product does not compete with ATP.
References
1)?Iwami et al. (1987), A new immunomodulator, FR-900494: taxonomy, fermentation, isolation, and physico-chemical and biological characteristics; J.Antibiot. (Tokyo) 40 612
2)?Elbein et al. (1990), Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I; ?J.Biol.Chem. 265 15599
3)?Bartoli et al. (2008), Mannosidase I inhibition rescues the human alpha-sarcoglycan R77C recurrent mutation; ?Hum.Mol.Genet. 17 1214
4)?Wang et al. (2011), Inhibition of endoplasmic reticulum-associated degradation rescues native folding in loss of function protein misfolding diseases; J.Biol.Chem. 286 43454
Check Digit Verification of cas no
The CAS Registry Mumber 109944-15-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,9,9,4 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 109944-15:
(8*1)+(7*0)+(6*9)+(5*9)+(4*4)+(3*4)+(2*1)+(1*5)=142
142 % 10 = 2
So 109944-15-2 is a valid CAS Registry Number.
InChI:InChI=1/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
109944-15-2Relevant articles and documents
Total Synthesis of (+)-Kifunensine, a Potent Glycosidase Inhibitor
Rouden, Jacques,Hudlicky, Tomas
, p. 1095 - 1098 (1993)
(+)-Kifunensine, a potent inhibitor of mannosidase I, has been synthesized in 13 steps from chlorobenzene by microbial oxygenation with Pseudomonas putida 39D and stereocontrolled peripheral functionalization of cis-3-chlorocylohexa-3,5-dienediol 3.
Synthesis method of mannosidase inhibitor Kifunensine
-
, (2019/10/04)
The invention provides a synthesis method of mannosidase inhibitor Kifunensine. L-gulonic acid-gamma-lactone, which is cheap and easily available, is taken as an initial raw material to efficiently obtain the Kifunensine through multi-step chemical conversion, the overall yield of the reaction is high, reagents used in the process are cheap and easily available, and multiple steps in the synthesis process can be fed by a one-pot method, so that the operation is simple and convenient, and the method has a better industrial prospect.
A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum α-mannosidase I
Hering, Kirk W.,Karaveg, Khanita,Moremen, Kelley W.,Pearson, William H.
, p. 9892 - 9904 (2007/10/03)
A practical synthesis of the potent class I α-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-diisop
Process for preparing kifunensine intermediate and kifunensine therefrom
-
Page 12, (2008/06/13)
A novel method for the preparation of a compound of formula (I) from an N-protected-D-mannosamine. A compound of formula (I) is a useful intermediate for the preparation of kiftnensine, a potent and selective mannosidase inhibitor. The method includes pro
Synthesis of kifunensine, an immunomodulating substance isolated from a microbial source
Kayakiri,Kasahara,Nakamura,Oku,Hashimoto
, p. 1392 - 1396 (2007/10/02)
Kifunensine (1), a novel immunomodulator isolated from an actinomycete, was enantiospecifically synthesized from D-mannosamine via a double cyclization of the oxamide-aldehyde precursor with ammonia as a key step. The absolute stereochemistry of natural kifunensine was confirmed to be the D form.
SYNTHESIS OF KIFUNENSINE, AN IMMUNOMODULATING SUBSTANCE ISOLATED FROM MICROBIAL SOURCE
Kayakiri, Hiroshi,Kasahara, Chiyoshi,Oku, Teruo,Hashimoto, Masashi
, p. 225 - 226 (2007/10/02)
A synthesis of kifunensine (1) has been achieved by a route involving, as a key step, a double cyclization of aldehyde 3 with ammonia.
