L-(+)-Cysteine → Butanol acetic acid water

HRID 1952695Notes

Reaction equation

HRID 1952695 reaction equation
[C:1]1(=O)N[C:4](=[O:6])[CH:3]=[CH:2]1.N[C@H:9]([C:12]([OH:14])=[O:13])CS>>[CH2:4]([OH:6])[CH2:3][CH2:2][CH3:1].[C:12]([OH:14])(=[O:13])[CH3:9].[OH2:6]

Participants

3

Reactant 2

HCID 5862L-(+)-CysteineHCID 10935Maleimide

Product 1

HCID 22056973Butanol acetic acid waterYield 15%

Procedure

A stable thioether bond forms when a sulfhydryl-containing peptide is reacted with the maleimide bearing intercalator as shown in Scheme 3 above. A sulfhydryl group may be attached to the N-terminal of the peptide with the reagent succinimidyl 3(2-pyridyldithio) propionate (Carlsson, J., et al., Biochem. 173:723 (1978)). Alternatively, the peptide may be synthesized with a cysteine residue at the appropriate location. The synthesis is robust and provides an overall yield of about 15%.

Workup

  1. customprovides an overall yield of about 15%

Sources & evidence

ORD record
ord-f562ff89caca48d5b16c26d90e77d506
Source dataset
uspto-grants-2000_09
Patent number
US06113946

Reaction notes

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