CAS 109944-15-2

Kifunensina, Kitasatosporia kifunense

Descrizione:

La kifunensina è un prodotto naturale derivato dall'actinobatterio Kitasatosporia kifunense, noto per il suo ruolo di potente inibitore dei processi di glicosilazione. È classificata come inibitore della mannosidasi, mirata specificamente all'enzima α-mannosidasi, che è cruciale nel processamento delle glicoproteine. Questa inibizione può influenzare vari percorsi biologici, rendendo la kifunensina uno strumento prezioso nella ricerca biochimica, in particolare negli studi relativi al ripiegamento delle proteine e alla glicosilazione. Il composto è caratterizzato dalla sua struttura complessa, che include più gruppi funzionali che contribuiscono alla sua attività biologica. La kifunensina ha suscitato interesse per le sue potenziali applicazioni in contesti terapeutici, in particolare nella ricerca sul cancro e nello studio delle infezioni virali, dove la glicosilazione gioca un ruolo significativo nelle interazioni patogeno-ospite. Inoltre, le sue proprietà uniche la rendono un argomento di interesse nel campo della chimica medicinale, dove comprendere il suo meccanismo d'azione potrebbe portare allo sviluppo di nuovi agenti terapeutici.

Formula: 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

InChI key: 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]

Sinonimi:

• (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

Formula: C₈H₁₂N₂O₆

Purezza: 98%

Colore e forma: Solid

Peso molecolare: 232.1907

Ref: IN-DA01CC21

Kifunensine

CAS: 109944-15-2

Kifunensine

Purezza: >99%

Colore e forma: Solid

Peso molecolare: 232.19g/mol

Ref: 54-BICL4125

Kifunensine

CAS: 109944-15-2

Formula: C₈H₁₂N₂O₆

Colore e forma: White To Off-White Solid

Peso molecolare: 232.19

Ref: 4Z-K-010002

Kifunensine-13C2,15N

CAS: 109944-15-2

Formula: C₆₁₃C₂H₁₂N₁₅NO₆

Peso molecolare: 235.17

Ref: 4Z-K-010003

Kifunensine

CAS: 109944-15-2

Formula: C₈H₁₂N₂O₆

Purezza: ≥ 99.0%

Colore e forma: White solid

Peso molecolare: 232.19

Ref: 7W-GC4430

Kifunensine

Prodotto controllato

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)

Formula: C₈H₁₂N₂O₆

Colore e forma: White To Off-White

Peso molecolare: 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.

Formula: C₈H₁₂N₂O₆

Purezza: Min. 99 Area-%

Colore e forma: Powder

Peso molecolare: 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.

Formula: C₈H₁₂N₂O₆

Purezza: Min. 95%

Colore e forma: White Powder

Peso molecolare: 232.19 g/mol

Ref: 3D-BK164600

Kifunensine-13C2 ,15N

Prodotto controllato

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);

Formula: C₂C₆H₁₂₁₅NNO₆

Colore e forma: Neat

Peso molecolare: 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.

Formula: C₈H₁₂N₂O₆

Peso molecolare: 232.19

Ref: TM-T20628