L-(+)-Cysteine → N-Acetyl-L-Cysteine

HRID 1836925Notes

Reaction equation

HRID 1836925 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].C(O)[C@H]1[O:14][C@H:13](OC2[C@H](O)[C@H](O)C(O)[C@H](O)[C@H]2O)[C@H:12]([NH3+])[C@@H](O)[C@@H]1O.P(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.C(S)[C@@H](O)[C@H](O)CS>P([O-])([O-])([O-])=O.C(O)[C@H]1O[C@H](OC2[C@H](O)[C@H](O)C(O)[C@H](O)[C@H]2O)[C@H](NC([C@@H]([NH3+])CS)=O)[C@@H](O)[C@@H]1O>[NH:1]([C:13]([CH3:12])=[O:14])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4]

Participants

7

Reactant 4

HCID 5862L-(+)-CysteineHCID 59575'-AtpHCID 446094D-1,4-DithiothreitolHCID 46878468HCID 46878468, compound

Product 1

HCID 12035N-Acetyl-L-Cysteine

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 46878469HCID 46878469, compoundSolvent

Procedure

Incubation of 100 μM Cys and 50 μM GlcN-Ins with 1 mM ATP in phosphate buffer, pH 7.5, containing 1 DTT after addition of cell extract supernatant resulted in an increase in Cys-GlcN-Ins from <0.2 to 26 μM over 60 min while the MSH content declined from 15 to 13 μM, corresponding to the MSH content present in the undialyzed cell extract. A parallel experiment with 100 μM AcCys in place of Cys resulted in an increase from <0.2 to 20 μM Cys-GlcN-Ins, and no change in MSH content (15 μM); however, marked conversion of AcCys to Cys had occurred by 60 min ([Cys]/[AcCys]˜3). If the MSH had increased by as much as 2 μM (10% of the change in Cys-GlcN-Ins) the change would have been detected and this experiment therefore established that conversion of Cys to Cys-GlcN-Ins is at least an order of magnitude faster than conversion of AcCys to MSH under these conditions.

Workup

  1. additionafter addition of cell
  2. extractionextract supernatant
  3. customresulted in
  4. extractionextract

Sources & evidence

ORD record
ord-6b162d157f7f4cd49d4eb75183358910
Source dataset
uspto-grants-2004_08
Patent number
US06780418B1

Reaction notes

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