A rapid reaction releasing the carboxyl terminal residues of peptides

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7557-7560

  Yagisawa, Shiroki ^a   Urakami, Masako ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PEPTIDE SYNTHESIS; PROTEIN DEGRADATION; REACTION ANALYSIS;

EID: 0030583469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01716-9     Document Type: Article

References (19)

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10. 16. Acetyl leucine enkephalin was prepared by treating leucine enkephalin with 0.01 M acetic anhydride in THF containing 0.04 M N-methylmorpholine and purified by HPLC. ODS columns ( Toso 80TM ) were used in the analysis and the preparation.The solvents were dried with Molecular Sieves 3A.
11. 10. The reactions are usually completed in a few minutes and can be accelerated at higher HCl concentrations. 0.02M was chosen for the sake of the repetitive cycles which need the alkaline hydrolysis of the shortened peptide esters. The reaction requires water, but trace water in the solvents was enough for the reaction.
12. -1. Isobutyl-chloroformate formed oxazolones similarly, but dicyclohexyl carbodiimide and trifluoroacetic anhydride were less effective under the present conditions.The by-product was assigned to the 5-ethoxycarbonyloxy oxazole from FAB MS (M+1=305 ) formed by the acylation of the carbonyl oxygen by excess ECF. Murakami, M.; Iwanami, M. Bull.Chem.Soc.Jap. 1968, 41, 726-727
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