Nondenaturing zwitterionic detergents

Details Nondenaturing zwitterionic detergents Nondenaturing zwitterionic detergents

1981-08-19

1983-02-08

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

564193, C07J 900

Patent

active

043728880

ABSTRACT:
A nondenaturing zwitterionic detergent for proteins which, for example, consists of an effective amount of 3-[(3-chloamidopropyl)dimethylammonio]-1-propanesulfonate (CHAPS). This detergent is of extreme interest in the biological study of proteins due to its nondenaturing characteristic. Other examples of the group may be prepared from different alicyclic compounds, for example, utilizing cholic acid and in others deoxycholic acid and dehydroabietic acid. A process for the preparation of these compounds starts with cholic or the equivalent and from this is prepared the triethylammonium salt in tetrahydrofuran (THF). After the salt is completely dissolved in THF, ethyl chloroformate is added and the flask cooled to 0.degree. C. Then the mixed anhydride which forms is reacted with dimethylaminopropylamine to form the dimethylaminopropyl derivative of a carboxylic acid amide. Finally, the tertiary amine group is reacted with propanesultone to give the sulfobetaine product.
An improved procedure for preparation of these compounds and especially for the last step (as for CHAPSO) to react the N-(3-dimethylaminopropyl)cholamide with sodium-1-chloro-2-hydroxy-3-propanesulfonate.

REFERENCES:
patent: 3910888 (1975-10-01), Widauer et al.
patent: 4104285 (1978-08-01), Torres et al.
patent: 4264514 (1981-04-01), Hixson, Jr. et al.

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