Isopropylamine → Pyridoxal 5'-phosphate

HRID 1755207Notes

Reaction equation

HRID 1755207 reaction equation
NC(C)/[CH:3]=[CH:4]/[C:5]([NH:7][C@@H:8]1[CH2:13][C@H:12](C)[C@H:11](C/C=C(\C)/C=C/[C@H]2O[C@H](CC(N)=O)C[C@]3(OC3)C2)[O:10][C@@H:9]1C)=O.NC(C)/C=C\C(N[C@@H]1C[C@H](C)[C@H](C/C=C(\C)/C=C/[C@H]2O[C@H](CC(N)=O)C[C@]3(OC3)C2)O[C@@H]1C)=[O:40].[P:69]([O-:73])([O-:72])([O-:71])=[O:70].[Na+].[Na+].[Na+].C(N)(C)C>CS(C)=O.P([O-])([O-])([O-])=O>[CH3:9][C:8]1[N:7]=[CH:5][C:4]([CH2:3][O:70][P:69]([OH:73])([OH:72])=[O:71])=[C:12]([CH:11]=[O:10])[C:13]=1[OH:40].[P:69]([O-:73])([O-:72])([O-:71])=[O:70]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 24243Trisodium PhosphateHCID 86718416HCID 86718416, compoundHCID 86718417HCID 86718417, compound

Product 2

HCID 1051Pyridoxal 5'-phosphateHCID 1061Phosphate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1061PhosphateSolvent

Procedure

Synthesis of (2E)-4-amino-N-[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3S,5S,7S)-7-(2-amino-2-oxoethyl)-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]pent-2-enamide (#B271) and (2Z)-4-amino-N-[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3S,5S,7S)-7-(2-amino-2-oxoethyl)-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]pent-2-enamide (#B272): To 100 mM sodium phosphate buffer pH 7.4 (3.57 ml) were added #B129 (7 mg, in 0.23 ml DMSO, 1 eq.), isopropylamine (1.475 ml of a 1 M solution made in phosphate buffer pH 3, giving a solution of pH ˜7, 100 eq.), pyridoxal phosphate (0.295 ml of a 50 mM solution in phosphate buffer pH 7.4, 1 eq.), and ATA-P2-B01 enzyme preparation (33 mg, in 0.33 ml phosphate buffer pH 7.4, Codexis, lot #D11134, R-selective for acetophenone). After incubation at 30° C., 200 rpm for 19 hours, pH was adjusted to ˜12 with sodium hydroxide and the reaction was extracted seven times with equal volume of ethylacetate. The solvent was evaporated under reduced pressure, the residue resuspended in 0.25 ml acetonitrile/water 1:1, filtered and purified by reverse phase chromatography in a total of 10 runs (Method I). The fractions with retention time of 10 and 13 min were collected and neutralized with ammonium hydroxide before freeze-drying to afford #B271 and #B272, respectively, as white solids.

Sources & evidence

ORD record
ord-6e816371473b498fac276ac3a98f9295
Source dataset
uspto-grants-2015_10
Patent number
US09169264B2

Reaction notes

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