L-Lysine → L-Leucine

HRID 1446968Notes

Reaction equation

HRID 1446968 reaction equation
N[C@H](C(O)=O)CCCCN.N[C@H](C(O)=O)C.N[C@H](C(O)=O)CCCCN.[NH2:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][C:30]1[CH:35]=CC=C[CH:31]=1.N[C@H](C(O)=O)CCCCN>>[NH2:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][CH:30]([CH3:35])[CH3:31]

Participants

4

Reactant 3

HCID 5962L-LysineHCID 168589Alanine--lysine (1/1)2×HCID 22822835Poly(lysine, phenylalanine)

Product 1

HCID 6106L-Leucine

Procedure

These compounds were prepared from the corresponding compounds I-III by removal of protecting groups with HBr in acetic acid. The benzyloxycarbonyl and t-butyloxycarbonyl groups were simultaneously removed by treatment with 30% Hbr in acetic acid containing anisol (10%) for 15 minutes at room temperature. Yields were about 90%. The molar ratios of the constituent amino acid residues and electrophoretic migrations relative to lysine were for compounds IV: Ala/Lys=1.05 (calc. 1.00), RLys =0.55, for compound V: Phe/Lys=1.06 (calc. 1.00), RLys =0.46, for compound VI: Ala/Lys=1.98 (calc. 2.00); RLys =0.51. Incubation of each of the compounds IV, V and VI with leucine aminopeptidase (E.C. 3.4.11.1) produced quantitatively ε(2-aminobenzoyl)-L-lysisne, (RLys =0.26) and the other expected product as judged by high voltage paper electrophoresis using authentic markers.

Workup

  1. customThese compounds were prepared from the corresponding compounds
  2. customby removal of protecting groups with HBr in acetic acid
  3. customThe benzyloxycarbonyl and t-butyloxycarbonyl groups were simultaneously removed by treatment with 30% Hbr in acetic acid
  4. additioncontaining anisol (10%) for 15 minutes at room temperature
  5. customYields

Sources & evidence

ORD record
ord-230e62eed89648d0b4ad45b9b9050588
Source dataset
uspto-grants-1982_02
Patent number
US04314936

Reaction notes

Loading…