Ammonia → L-Glutamine

HRID 571160

Reaction equation

HRID 571160 reaction equation
Cl[CH:2]([CH3:15])[C:3]([NH:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][C:9](=[O:11])[NH2:10])=[O:4].[NH3:16]>>[NH2:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][C:9](=[O:11])[NH2:10].[NH2:16][C@H:2]([C:3]([NH:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][C:9](=[O:11])[NH2:10])=[O:4])[CH3:15]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 71368222N~2~-(2-Chloropropanoyl)-L-glutamine

Product 2

HCID 5961L-GlutamineHCID 123935L-Alanyl-L-Glutamine

Procedure

Alanylglutamine is prepared according to Chinese Patent CN1680428A. Wherein, N-α-chloropropionyl)-L-glutamine is synthesized first. Then, 0.12 g of the N-(α-chloropropionyl)-L-glutamine crystals containing two diastereomeric isomers and 300 mL of 28% aqueous ammonia are mixed in a reaction vessel under room temperature. The reaction is carried out under 60° C. temperature and 2 kg/cm2 pressure. L-Alanyl-L-glutamine crude product is obtained after workup procedures. TLC shows an Rf value of 0.14, with acetate:n-butanol:water (1:4:1) eluent and ninhydrin stain. The above L-alanyl-L-glutamine crude product is dissolved in water, charged with activated carbon, and stirred under room temperature. Then the activated carbon is filtered out, mother crystals are added into the solution, and the system is settled for a while.

Workup

  1. customAlanylglutamine is prepared
  2. additionare mixed in a reaction vessel under room temperature
  3. customis carried out under 60° C.

Sources & evidence

ORD record
ord-959c57ded5bb4670a7e46fd1f9528365
Source dataset
uspto-grants-2015_05
Patent number
US09024064B2

Linked notes

Loading…