Elsevier

Tetrahedron

Volume 35, Issue 21, 1979, Pages 2577-2582
Tetrahedron

Peptides—XXXII1: The use of phenyl esters in peptide synthesis

https://doi.org/10.1016/0040-4020(79)88023-0Get rights and content

Abstract

Phenyl esters of N-terminal amino-protected peptides are valuable intermediates in synthesis of polypeptides. The phenyl ester function is stable during the customary manipulations of chain extension, and it can be removed selectively by treatment with one equivalent of hydrogen peroxide at pH 10.5 in a variety of solvents such as 80% acetone, dimethylfonnamide, hexamethylphosphoramide or trifluoroethanol. The method has always been satisfactory providing that dimethylsulphide is used as a scavenger.

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  • Cited by (39)

    • Structure-activity relationship study of non-steroidal NPC1L1 ligands identified through cell-based assay using pharmacological chaperone effect as a readout

      2014, Bioorganic and Medicinal Chemistry
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      Bromination at the 6-position of 3,4-dihydro-2(1H)-quinolinone (88)30 and subsequent coupling with phenyl formate31 were conducted by employing reported reaction conditions. N-Alkylation, hydrolysis using hydrogen peroxide32,33 and condensation gave the desired compound. Although cycloalkaquinolinones corrected the localization of mutant NPC1L1, bicyclic compound (36) was inactive (Table 3).

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    1

    Part XXXI: A.J. Bates, I.J. Galpin, A. Hallet, D. Hudson, G. W. Kenner, R. Ramage and R.C. Sheppard, Helv. Chim. Acta58, 688 (1975).

    2

    Deceased, 25 June 1978.

    3

    Correspondence to: Department of Chemistry, UMIST, Sackville Street, Manchester.

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