1,3,5-Trineopentylbenzene. VII. Friedel-Crafts Reactions of 1,3,5-Trineopentylbenzene with Acyl Chlorides and Preparations of Some Chloro Derivatives of 1,3,5-Trineopentylbenzene.

The racemization of the liberated 7-[(N,N-dimethylamino)sulfonyl]-4-(2,1,3-benzoxadiazolyl)-thiazoli none (DBD-TZ) amino acid during the cyclization/cleavage reaction with trifluoroacetic acid (TFA) in the Edman sequencing procedure has been carefully investigated, and evidence is presented to show conclusively that the racemization is caused by the replacement of a hydrogen atom by TFA. The fluorescent reagent 7-[N,N-dimethylamino)sulfonyl]-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS) was used for amino acid sequencing, and DBD-TZ amino acid was used for sequence and configuration determination. DBD-thiocarbamoylated peptides were cyclized and cleaved with deuterated TFA, and the protonated pseudomolecular ions (M-d1 + H)+ of DBD-TZ amino acids were detected by LC/MS. Furthermore, in the reaction kinetics study, we confirmed that the replacement reaction by TFA correlated sufficiently with the racemization of DBD-TZ amino acids. For the purpose of retaining D/L-amino acid configuration in sequencing, we used an aprotic acid, i.e., the Lewis acid boron trifluoride (BF3), for the cyclization/cleavage reaction. When we used BF3, the derivatized DBD-TZ amino acid was scarcely racemized under cyclization/cleavage conditions. Using this method, amino acid sequencing of D-Phe-Met-Arg-Phe-amide could be performed, retaining the D/L-configuration of the amino acid residues.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

1,3,5-Trineopentylbenzene. VII. Friedel-Crafts Reactions of 1,3,5-Trineopentylbenzene with Acyl Chlorides and Preparations of Some Chloro Derivatives of 1,3,5-Trineopentylbenzene.

Cited by 2 publications

References 0 publications

ChemInform Abstract: 1,3,5‐TRINEOPENTYLBENZENE PART 7, FRIEDEL‐CRAFTS REACTIONS OF 1,3,5‐TRINEOPENTYLBENZENE WITH ACYL CHLORIDES AND PREPARATIONS OF SOME CHLOR DERIVATIVES OF 1,3,5‐TRINEOPENTYLBENZENE

ChemInform Abstract: 1,3,5‐TRINEOPENTYLBENZENE PART 7, FRIEDEL‐CRAFTS REACTIONS OF 1,3,5‐TRINEOPENTYLBENZENE WITH ACYL CHLORIDES AND PREPARATIONS OF SOME CHLOR DERIVATIVES OF 1,3,5‐TRINEOPENTYLBENZENE

Proton: A Major Factor for the Racemization and the Dehydration at the Cyclization/Cleavage Stage in the Edman Sequencing Method

Contact Info

Product

Resources

About