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Nondenaturing zwitterionic detergents
| Details |
Inventors: Hjelmeland, Leonard M.;
Assignee: The United States of America as represented by the Secretary of the (Washington, DC)
Primary Examiner: Roberts; Elbert L.
Assistant Examiner:
Attorney, Agent or Firm: Roberts, Jr.; John S.
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. |
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DETAILED DESCRIPTION I claim: 1. A nondenaturing zwitterionic detergent for protein consisting of an effective amount of 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate in a water carrier. 2. The process according to claim 1 of producing 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate. 3. The compound 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate. 4. The process according to claim 1 of producing 3-[(3-cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate. 5. The compound 3-[(3-cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate. 6. A process for producing a nondenaturing zwitterionic detergent for protein derived from the reaction of an acid selected from one member of a group of carboxylic acids consisting of cholic acid, deoxycholic acid, and dehydroabietic acid reacted with a polyethyleneamine selected from one member of the group consisting of ##STR8## or reacted with a polypropyleneamine selected from one member of the group consisting of ##STR9## and reacted with an alkylating agent selected from one member of the group consisting of propanesultone, butanesultone, sodium 3-Cl,2-OH-propanesulfonate, sodium 2-Br-ethane sulfonate, and sodium chloroacetate wherein (1) said carboxylic acid is reacted with an amine to form a triethylammonium salt in the solvent tetrahydrofuran; (2) after the salt is completely dissolved, ethyl chloroformate is added and the flask is cooled to 0. degree. C. and a precipitate forms which is triethylamine hydrochloride which is filtered away from the mixed anhydride; (3) the product, mixed anhydride, reacts with a polyamine to form the polyamine derivative of a carboxylic acid amide as well as ethanol and carbon dioxide by products; (4) the polyamine is reacted with an alkylating agent selected from one member of the group consisting of ##STR10## to give the betaine.
Description:
This invention relates to a nondenaturing zwitterionic detergent for proteins which, for example, consists of an effective amount of 3-[(3-chloamidopropyl)-dimethylammonio]-1-propanesulfonate (CHAPS)
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