Abstract: A sequencing method which exploits the thioacylation degradation of polypeptides and proteins is disclosed. The process involves reaction of the N-terminal amino acid of a polypeptide with an excess of a thioacylating reagent. After sufficient time to insure quantitative coupling and removal of excess reagent, the N-thioacyl polypeptide is subjected to cleavage by acid which affords a 2-substituted-5(4H)-thiazolinone of the N-terminal amino acid. Subsequent addition of a large excess of an aliphatic primary or secondary alcohol, either directly to the cleavage acid or after its removal, yields the corresponding N-thioacyl amino acid ester, a stable compound suitable for chromatographic separation and subsequent detection by contemporary methods of high pressure liquid chromatography.

Abstract: A protein micro sequencing method for use in conjunction with the thiocylation degradation of polypeptides and proteins is disclosed. The process involves reaction of the N-terminal amino acid of a polypeptide with an excess of a thioacylating reagent. After sufficient time to insure quantitative coupling and removal of excess reagent, the derivatized polypeptide is subjected to cleavage by acid which affords a 2-substituted-5(4H)-thiazolinone. After removal of excess acid, the thiazolinone is reacted with a small excess of a fluorescent or enhanced ultraviolet absorbance reagent having a reactive carboxylic acid chloride, sulfonic acid chloride, chloroformate, isocyanate or anhydride functionality, in the presence of a tertiary amine catalyst, to yield the corresponding 5-O-acyl-2-(substituted)thiazole derivative, detectible by enhanced ultravoilet absorobance or fluorescence emission at extremely low concentration thereby providing a method of sequencing very small amounts of protein.

Abstract: A solid phase N-hydroxysuccinimide reagent having the general formula: ##STR1## where X is particulate silica gel or controlled pore glass; n=3-7; Y is either (CH.sub.2).sub.n' or (CH.sub.2).sub.n' --NH--CO--CH.sub.2 wherein n'=2-6; Z may be in the form of OCOR, OSO.sub.2 R and OCO.sub.2 R, and Z' may be either Z or OH, wherein R is a chromophore, fluorophore or electrophore capable of detection in chromatographic separation technology is disclosed. Also disclosed is the method for making compounds of this type and the method for using these compounds to identify and quantitate analytes having primary or secondary amine or thiol functionalities.

Abstract: A solid phase oxime compound having the general formula: ##STR1## where X is particulate silica gel or controlled pore glass; n is 3 or 4, n' is 1-6; R' is an electron withdrawing group; and Y and Y' are selected from OH, OCOR", OSO.sub.2 R" and OCO.sub.2 R", where R" is a chromophore, fluorophore or electrophore, is disclosed. Also disclosed is the method for making compounds of this type and the method for using these compounds to detect and quantify analytes having primary or secondary amines or thiol functionalities.