Glyoxylic Acid → N,N,N',N'-tetrakis(carboxymethyl)-L-cystine

HRID 1668264Notes

Reaction equation

HRID 1668264 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[CH2:6]([S:12][S:13][CH2:14][C@H:15]([NH2:19])[C:16]([OH:18])=[O:17])[C@H:7]([NH2:11])[C:8]([OH:10])=[O:9].B([O-])([O-])[O-]>>[C:1]([CH2:2][N:11]([CH2:2][C:1]([OH:5])=[O:4])[C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][S:12][S:13][CH2:14][C@H:15]([N:19]([CH2:15][C:16]([OH:18])=[O:17])[CH2:7][C:8]([OH:10])=[O:9])[C:16]([OH:18])=[O:17])([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 760Glyoxylic AcidHCID 26574BorateHCID 67678(-)-Cystine

Product 1

HCID 11259991N,N,N',N'-tetrakis(carboxymethyl)-L-cystine

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-43212e86a7de40509f16f4ddc680d297
Source dataset
uspto-grants-2011_08
Patent number
US07988858B2

Reaction notes

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