Carbon Dioxide → [(4S,6R,9E,11R,12R)-11-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-4-[(4R)-2-oxo-1,3-dioxolan-4-yl]-5-oxatricyclo[8.3.0.04,6]trideca-1(13),9-dien-2,7-diyn-12-yl] 7-methoxy-5-methylnaphthalene-1-carboxylate

HRID 1012889

Reaktionsgleichung

Reaktionsgleichung von HRID 1012889
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])O)[OH:8])[OH:6])[OH:4].[C:13]([O-])(=O)[C:14]([CH3:16])=O.CC1(C)S[C@@H]2[C@H](N[C:29]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:30])C(=O)N2[C@H]1C([O-])=O.[K+].C[C@@H]1O[C@@H:47]([O:49][C@H:50]2[C@H:55](O)[C@@H:54](O)[C@H:53](NC(N)=N)[C@@H:52](O)[C@@H:51]2NC(N)=N)[C@H:46]([O:67][C@@H:68]2[O:73][C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2NC)[C@@:45]1([OH:82])C=O.C[C@H](N)[C:85]([NH:87][C@H](C(O)=O)CCC(N)=O)=O.[C:98](=O)=O.CC[C:103]([O:105][C:106]1([C:113]2[CH:118]=[CH:117][CH:116]=CC=2)CCN(C)CC1)=[O:104]>>[CH3:13][C:14]1[C:37]2=[CH:36][CH:35]=[CH:34][C:33]([C:103]([O:105][C@H:106]3[C@H:51]([O:12][C@H:11]4[O:4][C@H:3]([CH3:2])[C@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]4[NH:87][CH3:85])[C:52]4=[CH:53][C:54]#[C:55][C@H:50]5[O:49][C@@:47]5([C@@H:46]5[O:67][C:68](=[O:73])[O:82][CH2:45]5)[C:116]#[C:117][C:118]4=[CH:113]3)=[O:104])=[C:32]2[CH:31]=[C:29]([O:30][CH3:98])[CH:16]=1

Komponenten

8

Edukt 7

HCID 280Carbon DioxideHCID 615834-propionyloxy-4-phenyl-N-methylpiperidineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 107735PyruvateHCID 123935L-Alanyl-L-GlutamineHCID 23664709Penicillin G PotassiumHCID 178484872HCID 178484872, Verbindung

Produkt 1

HCID 44581473[(4S,6R,9E,11R,12R)-11-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-4-[(4R)-2-oxo-1,3-dioxolan-4-yl]-5-oxatricyclo[8.3.0.04,6]trideca-1(13),9-dien-2,7-diyn-12-yl] 7-methoxy-5-methylnaphthalene-1-carboxylate

Versuchsvorschrift

Human cervix adenocarcinoma HeLa cells are maintained as exponentially growing monolayers in Dulbecco modified Eagle's minimum essential medium with 4.5 g/l glucose, 0.1 g/l pyruvate, 105 Ul/l penicilline, 0.1 g/l streptomycine, 0.86 g/l Glutamax I and 10% v/v foetal calf serum (37° C., 5% CO2), without or with 5 μM DL-threo-1-phenyl-2-hexadecanoyl-amino-3-morpholino-1-propanol (PPMP) to inhibit Gb3 expression. When present, PPMP is introduced into pre-cultures for at least 6 days prior to cytotoxicity assays and is present for up to drug wash.

Aufarbeitung

  1. temperatureHuman cervix adenocarcinoma HeLa cells are maintained as exponentially growing monolayers in Dulbecco
  2. washwash

Quellen und Nachweise

ORD-Eintrag
ord-23c0a3b0201b491e9456e3b03f934fbf
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981400B2

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