Succinic Acid → Alpha-Cyano-4-Hydroxycinnamic Acid

HRID 2227123Notes

Reaction equation

HRID 2227123 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[NH2:11][C@H:12](C(O)=O)CC1C2C(=CC=CC=2)NC=1.O=[CH:27][C@@H:28]([C@H:30]([C@H:32]([C@@H:34](CO)O)O)[OH:31])O.N[C@H](C(O)=O)[C@@H](C)O.OP([O-])(O)=O.[K+].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.N[C@H](C(O)=O)CC(C)C.N[C@H](C(O)=O)CC1N=CNC=1>>[C:12]([C:3](=[CH:2][C:1]1[CH:34]=[CH:32][C:30]([OH:31])=[CH:28][CH:27]=1)[C:4]([OH:6])=[O:5])#[N:11]

Participants

10

Reactant 9

HCID 1110Succinic AcidHCID 6106L-LeucineHCID 6288L-ThreonineHCID 6305L-TryptophanHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178419078HCID 178419078, compound

Product 1

HCID 2102Alpha-Cyano-4-Hydroxycinnamic Acid

Procedure

SC-H agar: 7.5 g/l yeast nitrogen base without amino acids, 11.3 g/l succinic acid, 6.8 g/l NaOH, 5.6 g/l casamino acids without vitamins, 0.1 g/l tryptophan, and 20 g/l agar (Bacto). Autoclaved for 20 min. at 121° C. After autoclaving, 55 ml of a 22% galactose solution and 1.8 ml of a 5% threonine solution were added per 450 ml agar. YNB-1 agar: 3.3 g/l KH2PO4, 16.7 g/l agar, pH adjusted to 7. Autoclaved for 20 min. at 121° C. After autoclaving, 25 ml of a 13.6% yeast nitrogen base without amino acids, 25 ml of a 40% glucose solution, 1.5 ml of a 1% L-leucine solution and 1.5 ml of a 1% histidine solution were added per 450 ml agar.

Workup

  1. waitAutoclaved for 20 min. at 121° C

Sources & evidence

ORD record
ord-825e88adbf2b4870a7c292cc0810c294
Source dataset
uspto-grants-2002_07
Patent number
US06413559B1

Reaction notes

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