Reaction #2006453

ord-0d44b2af5d6a4911b01d20c5c4d4e38e

Reaction equation

[Na+].[OH-]
sodium hydroxide
CC(C)(C)OC(=O)N1CCCC(=O)C1
N-Boc-3-piperidinone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1
NAD+
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate
→
CC(C)(C)OC(=O)N1CCCCC1N
N-Boc-aminopiperidine

Reactants

—
resultant product
—
aqueous solution
[Na+].[OH-]
sodium hydroxide
CC(C)(C)OC(=O)N1CCCC(=O)C1
N-Boc-3-piperidinone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1
NAD+
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Other(pNTPSPAG), obtained in Example 10, which
  2. 2
    workup.ADDITIONwas added so that total volume was 30 ml

Procedure

To a flask containing 0.6 g of a substrate N-Boc-3-piperidinone, 0.82 g of D-glucose, 4 mg of NAD+, 1.62 g of L-alanine, and 4.0 mg of pyridoxal phosphate, a culture fluid of the recombinant E. coli HB101 (pNTPSPAG), obtained in Example 10, which expresses TPS, PALDH, and GDH was added so that total volume was 30 ml. The resultant product was stirred at 30° C. for 20 hours while being adjusted to a pH of 6.8 by drippage of 5 N aqueous solution of sodium hydroxide. The amount of N-Boc-aminopiperidine produced and the optical purity thereof were measured according to the method described in Example 19. In the result, the amount produced was 0.54 g. The absolute configuration of N-Boc-aminopiperidine was (S), and the optical purity was 99.4% e.e.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08168412B2uspto-grants-2012_05