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

Participants

Role	Name	HCID	Charge
Reactant	Carbon Dioxide	HCID 280	—
Reactant	4-propionyloxy-4-phenyl-N-methylpiperidine	HCID 61583	—
Reactant	(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal	HCID 107526	—
Reactant	Pyruvate	HCID 107735	—
Reactant	L-Alanyl-L-Glutamine	HCID 123935	—
Reactant	Penicillin G Potassium	HCID 23664709	—
Reactant	HCID 178484872	HCID 178484872	—
Product	[(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	HCID 44581473	—

Reaction Steps

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 UI/I 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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08313731B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-a449d31f377044ea8c25ee0c3d5d20a9
Source note	uspto-grants-2012_11