Pyridoxal 5'-phosphate → (R)-(+)-1-Boc-3-aminopyrrolidine

HRID 1919269Notes

Reaction equation

HRID 1919269 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+:30]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.N[C@@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[OH-].[Na+]>>[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:30])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 6

HCID 1051Pyridoxal 5'-phosphate2×HCID 5893Nadide (JAN/USAN/INN)HCID 14798Sodium HydroxideHCID 71080D-Alanine2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate2×

Product 1

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Procedure

To a flask containing 0.5 g of a substrate N-Boc-3-pyrrolidinone, 0.73 g of D-glucose, 4 mg of NAD+, 1.44 g of D-alanine, and 3.3 mg of pyridoxal phosphate, a culture fluid of the recombinant E. coli HB101 (pNTASPAG), obtained in Example 11, which expresses TAS, PALDH, and GDH was added so that total volume was 25 ml. The resultant product was stirred at 30° C. while being adjusted to a pH of 6.8 by drippage of 5 N aqueous solution of sodium hydroxide. After nine hours in reaction, 0.25 g of N-Boc-3-pyrrolidinone, 0.37 g of D-glucose, 0.37 g of D-alanine, and 3 mg of pyridoxal phosphate were added.

Workup

  1. custom(pNTASPAG), obtained in Example 11, which
  2. additionwas added so that total volume was 25 ml
  3. additionwere added

Sources & evidence

ORD record
ord-fc3e45df8de8430f9df416e5bd68e269
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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