Phenylmethylsulfonyl Fluoride → Coenzyme A

HRID 1871866Notes

Reaction equation

HRID 1871866 reaction equation
CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.N([S:48][CH2:49][CH2:50][NH:51][C:52](=[O:95])[CH2:53][CH2:54][NH:55][C:56](=[O:94])[C@H:57]([OH:93])[C:58]([CH3:92])([CH3:91])[CH2:59][O:60][P:61]([OH:90])(=[O:89])[O:62][P:63]([OH:88])(=[O:87])[O:64][CH2:65][C@H:66]1[O:70][C@@H:69]([N:71]2[C:80]3[N:79]=[CH:78][N:77]=[C:75]([NH2:76])[C:74]=3[N:73]=[CH:72]2)[C@H:68]([OH:81])[C@@H:67]1[O:82][P:83]([OH:86])([OH:85])=[O:84])[C@@H](CCC(N[C@H](C(NCC(O)=O)=O)CS)=O)C(O)=O.CC(C(O)C(NCCC(NCCS)=O)=O)(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(O)=O)(O)=O)C.[N+](C1C=CC(SSC2C=CC([N+]([O-])=O)=C(C=2)C(O)=O)=CC=1C(O)=O)([O-])=O.C1C=C2C(C(O)=O)=CC(C3C=C(C(O)=O)C4C(=CC=CC=4)N=3)=NC2=CC=1.C1(CS(F)(=O)=O)C=CC=CC=1.CC([C@@H](O)C(NCCC(NCCS)=O)=O)(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(O)=O)(O)=O)C>C(O)C(N)(CO)CO.Cl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].[Cu]>[CH3:92][C:58]([C@@H:57]([OH:93])[C:56]([NH:55][CH2:54][CH2:53][C:52]([NH:51][CH2:50][CH2:49][SH:48])=[O:95])=[O:94])([CH2:59][O:60][P:61]([O:62][P:63]([O:64][CH2:65][C@H:66]1[O:70][C@@H:69]([N:71]2[C:80]3[N:79]=[CH:78][N:77]=[C:75]([NH2:76])[C:74]=3[N:73]=[CH:72]2)[C@H:68]([OH:81])[C@@H:67]1[O:82][P:83]([OH:86])([OH:85])=[O:84])([OH:88])=[O:87])([OH:90])=[O:89])[CH3:91]

Participants

11

Reactant 7

HCID 4784Phenylmethylsulfonyl FluorideHCID 62545,5'-Dithiobis(2-nitrobenzoic Acid)HCID 71068Bicinchoninic acidHCID 439335[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphateHCID 444485Dephospho-coaHCID 493570RiboflavinHCID 86755643glutathionyl-coenzyme A

Product 1

HCID 87642Coenzyme A

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 93573Tromethamine hydrochlorideSolvent

Procedure

Reduced nicotinamide adenine dinucleotide phosphate (NADPH), riboflavin, flavin adenine mononucleotide (FMN), flavin adenine dinucleotide (FAD), coenzyme A disulfide, glutathionyl-coenzyme A mixed disulfide, 3'-dephospho coenzyme A, 5,5'-dithio-bis(2-nitrobenzoic acid) (DTNB), lysostaphin, bicinchoninic acid solution, 4% copper sulphate pentahydrate solution, 2',5'-adenosine diphosphate (ADP)-Sepharose®; and phenylmethylsulphonyl fluoride (PMSF) were from Sigma (Mississauga, ON). 3'-dephospho CoA was oxidized to the disulfide by incubation at room temperature overnight in Tris-HCl (20 mM), pH 9.0, containing copper (5 μM). 4,4'-phosphopantetheine was formed by incubation of CoA with nucleotide pyrophosphatase. The thiol was oxidized as described above, and the disulfide was purified by high performance liquid chromatography (HPLC). All other chemicals were of reagent grade or better and were used without further purification.

Sources & evidence

ORD record
ord-20e171cb10bc4349a82014739271f945
Source dataset
uspto-grants-2000_08
Patent number
US06107068

Reaction notes

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