Peptide research 1995-01-01

Cleavage and deprotection of peptide resins using chloro- and bromotrialkylsilanes.

J L Hughes, E J Leopold

Index: Pept. Res. 8(5) , 298-300, (1995)

Full Text: HTML

Abstract

The cleavage of a peptide resin attached to a phenylacetomidomethyl (PAM) resin was investigated using bromotrimethylsilane (TMSBr) with thioanisole in trifluoroacetic acid (TFA), and by chlorotrimethylsilane (TMSCl) in the same reagents with lithium bromide. Both TMSBr and TMSCl cleaved the peptide from the resin, but TMSCl required elevated temperature (50 degrees C) to effect the cleavage. Procedures were investigated for the deprotection and cleavage of either N(g)-tosyl (Tos)- or mesitylenesulfonyl (MTS)-arginine residues attached to 4-methylbenzylhydrylamine (MBHA) resin, and of a peptide containing an MTS-arginine residue attached to MBHA resin, using either TMSCl or TMSBr as cleavage reagents. The MTS group is cleanly removed from arginine using TMSBr with thioanisole in TFA and by TMSCl in the same reagents with lithium bromide.

Related Compounds

  • Bromo(trimethyl)si...

Related Articles:

EPR and NMR spectroscopies provide input on the coordination of Cu(I) and Ag(I) to a disordered methionine segment.

2015-06-01

[J. Biol. Inorg. Chem. 20 , 719-27, (2015)]

Position and length of fatty acids strongly affect receptor selectivity pattern of human pancreatic polypeptide analogues.

2014-11-01

[ChemMedChem 9(11) , 2463-74, (2014)]

Reduced vascular endothelial growth factor and capillary density in the occipital cortex in dementia with Lewy bodies.

2014-07-01

[Brain Pathol. 24(4) , 334-43, (2014)]

Two-step hard acid deprotection/cleavage procedure for solid phase peptide synthesis.

1991-02-01

[Int. J. Pept. Protein Res. 37(2) , 145-52, (1991)]

The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide.

2008-06-21

[Org. Biomol. Chem. 6(12) , 2168-72, (2008)]

More Articles...