Benzoate → Phenylglycine, D-

HRID 2208639Notes

Reaction equation

[C:1]1(C([O-])=O)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[NH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[CH3:12].C(N)(C)C.P([O-])([O-])([O-])=O>>[CH:1]1[CH:6]=[CH:5][C:12]([C@@H:11]([NH2:10])[C:13]([OH:15])=[O:14])=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 242Benzoate

HCID 1061Phosphate

HCID 6363Isopropylamine

HCID 71080D-Alanine

Product 1

HCID 70134Phenylglycine, D-

Procedure

D-phenylglycine was produced with a conversion of 98% by conducting reactions using 50 mL of a mixture of 0.3 M phenylformate, 20 mM D-alanine, 0.45 M isopropylamine, 0.5 mM PLP, 50 mM phosphate pH 8, 35 U/mL DATA and 30 U/mL ARmutTA. 2.02 g of pure D-phenylglycine was obtained through purification based on solubility.

Sources & evidence

ORD record: ord-c816f87e965e4f679e595515d41bfcb8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376694B2

Reaction notes

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