CAS 109944-15-2

Kifunensina, Kitasatosporia kifunense

Descrição:

Kifunensina é um produto natural derivado do actinobactério Kitasatosporia kifunense, conhecido por seu papel como um potente inibidor dos processos de glicosilação. É classificada como um inibidor de mannosidase, direcionando-se especificamente à enzima α-mannosidase, que é crucial no processamento de glicoproteínas. Essa inibição pode afetar várias vias biológicas, tornando a kifunensina uma ferramenta valiosa na pesquisa bioquímica, particularmente em estudos relacionados ao dobramento de proteínas e glicosilação. O composto é caracterizado por sua estrutura complexa, que inclui múltiplos grupos funcionais que contribuem à sua atividade biológica. A kifunensina despertou interesse por suas potenciais aplicações em contextos terapêuticos, particularmente na pesquisa do câncer e no estudo de infecções virais, onde a glicosilação desempenha um papel significativo nas interações patógeno-hospedeiro. Além disso, suas propriedades únicas a tornam um assunto de interesse no campo da química medicinal, onde entender seu mecanismo de ação pode levar ao desenvolvimento de novos agentes terapêuticos.

Fórmula: C₈H₁₂N₂O₆

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

Chave InChI: InChIKey=OIURYJWYVIAOCW-PQMKYFCFSA-N

SMILES: C(O)[C@H]1N2[C@@]([C@@H](O)[C@@H](O)[C@@H]1O)(NC(=O)C2=O)[H]

Sinónimos:

• (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione
• (5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)imidazo[1,2-a]pyridine-2,3-dione
• Fr 900494
• Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-
• Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, [5R-(5α,6β,7α,8α,8aα)]-
• Kifunensine
• (5R,8aS)-1,5,6,7,8,8a-Hexahydro-6β,7α,8α-trihydroxy-5α-(hydroxymethyl)imidazo[1,2-a]pyridine-2,3-dione
• [5R-(5α,6β,7α,8α,8aα)]-
• Hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a] pyridine-2,3-dione
• KIFUNENSINE, KITASATOSPORIA KIFUNENSE
• FR 900494, Hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a] pyridine-2,3-dione
• Imidazo1,2-apyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-

Imidazo[1,2-a]pyridine-2,3-dione,hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-

CAS: 109944-15-2

Fórmula: C₈H₁₂N₂O₆

Pureza: 98%

Cor e Forma: Solid

Peso molecular: 232.1907

Ref: IN-DA01CC21

Kifunensine

CAS: 109944-15-2

Kifunensine

Pureza: >99%

Cor e Forma: Solid

Peso molecular: 232.19g/mol

Ref: 54-BICL4125

Kifunensine

CAS: 109944-15-2

Fórmula: C₈H₁₂N₂O₆

Cor e Forma: White To Off-White Solid

Peso molecular: 232.19

Ref: 4Z-K-010002

Kifunensine-13C2,15N

CAS: 109944-15-2

Fórmula: C₆₁₃C₂H₁₂N₁₅NO₆

Peso molecular: 235.17

Ref: 4Z-K-010003

Kifunensine

CAS: 109944-15-2

Fórmula: C₈H₁₂N₂O₆

Pureza: ≥ 99.0%

Cor e Forma: White solid

Peso molecular: 232.19

Ref: 7W-GC4430

Kifunensine

Produto Controlado

CAS: 109944-15-2

Stability Desiccate and Store at -20°C
Applications Kifunensine is an alkaloid produced by the fungus, Kitasatosporia kifunense, and has been shown to be a weak inhibitor of aryl mannosidase. It is a unique oxamide derivative of mannojirimycin and a potent inhibitor of the glycoprotein processing enzyme mannosidase I. Kifunenesine is ineffective in inhibiting either mannosidase II or the endoplasmic reticulum (ER) a-mannosidase. It also possesses immunomodulating properties based on chemical, physicochemical and x-ray crystallographic analysis.When tested in cell culture using influenza virus-infected MDCK cells, kifunensine, at 1 mg/ml or less, caused almost complete inhibition of complex chain formation with the accumulation of Man9(GlcNAc)2. Thus, kifunensine was proven to be 50 to 100 times more effective than deoxymannojirimycin.Ph
References Iwami, M., et al.: J. Antibiotic., 40, 612 (1987); Elbein, A.D., et al.: J. Biol. Chem., 265, 15599 (1990); Elbein, A.D., et al.: Archives of Biochem & Biophys., 288, 1, 177 (1991); Kayakiri, H., et al.: Chem. Pharm. Bull., 39(6), 1378 (1991)

Fórmula: C₈H₁₂N₂O₆

Cor e Forma: White To Off-White

Peso molecular: 232.19

Ref: TR-K450000

Kifunensine

CAS: 109944-15-2

Kifunensine is a potent and specific inhibitor of plant and animal α-mannosidase I with IC50 in nanomolar range. It inhibits the enzyme isoforms in Golgi apparatus (GMI) and endoplasmatic reticulum (ERMI). The compound prevents mannose trimming on glycoproteins and shifts the glycoform content from complex to oligomannose type. It's used for the production of recombinant therapeutic glycoproteins with mannose rich N-linked glycans.

Fórmula: C₈H₁₂N₂O₆

Pureza: Min. 99 Area-%

Cor e Forma: Powder

Peso molecular: 232.19 g/mol

Ref: 3D-MK10316

Kifunensine - Bio-X ™

CAS: 109944-15-2

Kifunensine is a small molecule inhibitor that was designed and synthesized to inhibit plant and animal α-mannosidase I. It is a potent and specific inhibitor with IC50 in nanomolar range. It inhibits the enzyme isoforms in Golgi apparatus (GMI) and endoplasmatic reticulum (ERMI). The compound prevents mannose trimming on glycoproteins and shifts the glycoform content from complex to oligomannose type. Used for the production of recombinant therapeutic glycoproteins with mannose rich N-linked glycans.

Fórmula: C₈H₁₂N₂O₆

Pureza: Min. 95%

Cor e Forma: White Powder

Peso molecular: 232.19 g/mol

Ref: 3D-BK164600

Kifunensine-13C2 ,15N

Produto Controlado

CAS: 109944-15-2

Applications Kifunensine-13C2 ,15N, is the labeled analogue of Kifunensine (K450000), which is a potent inhibitor of the mannosidase I enzyme and is primarily used in cell culture to make high mannose glycoproteins.
References Iwami, M., et al.: J. Antibiotic., 40, 612 (1987); Elbein, A.D., et al.: J. Biol. Chem., 265, 15599 (1990); Elbein, A.D., et al.: Archives of Biochem & Biophys., 288, 1, 177 (1991); Kayakiri, H., et al.: Chem. Pharm. Bull., 39(6), 1378 (1991);

Fórmula: C₂C₆H₁₂₁₅NNO₆

Cor e Forma: Neat

Peso molecular: 235.169

Ref: TR-K450002

Kifunensine

CAS: 109944-15-2

Kifunensine, an alkaloid, a glycosylation pathway inhibitor and immunomodulator. It strongly inhibits α-mannosidase I.

Fórmula: C₈H₁₂N₂O₆

Peso molecular: 232.19

Ref: TM-T20628