Réaction #1755446

ord-43212e86a7de40509f16f4ddc680d297

Équation de réaction

O=CC(=O)O
glyoxylic acid
N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O
L-cystine
[O-]B([O-])[O-]
borate
→
O=C(O)CN(CC(=O)O)[C@@H](CSSC[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O)C(=O)O
N,N,N′,N′-tetrakis(carboxymethyl)-L-cystine

Réactifs

O=CC(=O)O
glyoxylic acid
N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O
L-cystine
[O-]B([O-])[O-]
borate

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe alternative route, relying on in-solution phase synthesis of an intermediate product
  2. 2
    Autrepurified with ion exchange chromatography

Mode opératoire

The alternative route, relying on in-solution phase synthesis of an intermediate product starts with addition of a large excess (40 times) of glyoxylic acid to L-cystine in an alkaline borate buffer. The intermediate product, following pH manipulation and conductivity adjustment of the reaction mixture, purified with ion exchange chromatography to give N,N,N′,N′-tetrakis(carboxymethyl)-L-cystine.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07988858B2uspto-grants-2011_08