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The p-(methylsulfinyl)benzyl group: A TFA-stable carboxyl-protecting group readily convertible to a TFA-labile group
Year:
1988
Source of publication :
Journal of Organic Chemistry
Authors :
Brandeis, Ester
;
.
Volume :
53
Co-Authors:
Samanen, J.M., Peptide Chemistry Department, Smith Kline and French Laboratories, 709 Swedeland Road, Swedeland, PA 19479, United States
Brandeis, E., Peptide Chemistry Department, Smith Kline and French Laboratories, 709 Swedeland Road, Swedeland, PA 19479, United States
Facilitators :
From page:
561
To page:
569
(
Total pages:
9
)
Abstract:
The p-(methylsulfinyl)benzyl or Msib ester is recommended as a selectively cleavable carboxyl-protecting group for peptide synthesis. Peptide or amino acid esters of p-(methylsulfinyl)benzyl alcohol, HO-Msib (2), or p-(methylthio)benzyl alcohol, HO-Mtb (1), are readily prepared from the corresponding alcohols or alkyl halides. Msib esters may also be obtained from Mtb esters by oxidation with m-chloroperbenzoic acid. Msib esters are readily deoxygenated by excess Me3SiCl/Ph3P, Me3SiCl/Me2S, or anhydrous hydrogen chloride. Msib esters are exceedingly stable to TFA while Mtb esters solvolyze rapidly. A sample peptide synthesis demonstrates the protection of the C-terminal carboxyl group during synthesis as the Msib ester followed by Msib group removal on completion of synthesis by deoxygenation and TFA solvolysis. The stability of Mtb and Msib esters to typical acid conditions of peptide synthesis is described. The stability of Msib esters to various peptide synthesis conditions suggests that the Msib group should be quite useful as a carboxyl-protecting group in peptide synthesis. © 1988 American Chemical Society.
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DOI :
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Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
21314
Last updated date:
02/03/2022 17:27
Creation date:
16/04/2018 23:43
Scientific Publication
The p-(methylsulfinyl)benzyl group: A TFA-stable carboxyl-protecting group readily convertible to a TFA-labile group
53
Samanen, J.M., Peptide Chemistry Department, Smith Kline and French Laboratories, 709 Swedeland Road, Swedeland, PA 19479, United States
Brandeis, E., Peptide Chemistry Department, Smith Kline and French Laboratories, 709 Swedeland Road, Swedeland, PA 19479, United States
The p-(methylsulfinyl)benzyl group: A TFA-stable carboxyl-protecting group readily convertible to a TFA-labile group
The p-(methylsulfinyl)benzyl or Msib ester is recommended as a selectively cleavable carboxyl-protecting group for peptide synthesis. Peptide or amino acid esters of p-(methylsulfinyl)benzyl alcohol, HO-Msib (2), or p-(methylthio)benzyl alcohol, HO-Mtb (1), are readily prepared from the corresponding alcohols or alkyl halides. Msib esters may also be obtained from Mtb esters by oxidation with m-chloroperbenzoic acid. Msib esters are readily deoxygenated by excess Me3SiCl/Ph3P, Me3SiCl/Me2S, or anhydrous hydrogen chloride. Msib esters are exceedingly stable to TFA while Mtb esters solvolyze rapidly. A sample peptide synthesis demonstrates the protection of the C-terminal carboxyl group during synthesis as the Msib ester followed by Msib group removal on completion of synthesis by deoxygenation and TFA solvolysis. The stability of Mtb and Msib esters to typical acid conditions of peptide synthesis is described. The stability of Msib esters to various peptide synthesis conditions suggests that the Msib group should be quite useful as a carboxyl-protecting group in peptide synthesis. © 1988 American Chemical Society.
Scientific Publication
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