Source:http://linkedlifedata.com/resource/pubmed/id/11558592
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
9
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pubmed:dateCreated |
2001-9-17
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pubmed:abstractText |
As an extension of our investigation of peptidyl-resin linkage stability towards different cleavage procedures used in the solid-phase peptide synthesis (SPPS) technique, the present paper evaluated the trifluoromethanesulfonic acid (TFMSA)/trifluoroacetic acid (TFA)/thioanisole method, varying the type of resin (benzhydrylamine-resin, BHAR; methylbenzhydrylamine-resin, MBHAR and 4-(oxymethyl)-phenylacetamidomethyl-resin, PAMR) and peptide resin-bound residue (Gly and Phe). The vasoactive angiotensin II (AII, DRVYIHPF) and its [Gly8]-AII analogue linked to those resins used routinely in tert-butyloxycarbonyl (Boc)-SPPS chemistry were submitted comparatively to a time course study towards TFMSA/TFA cleavage. At 0 degrees C, [Gly8]-AII was completely removed from all resins in less than 6 h, but the hydrophobic Phe8 moiety-containing AII sequence was only partially cleaved (not more than 15%) from BHAR or MBHAR in this period. At 25 degrees C, [Gly8]-AII cleavage time decreased to less than 2 h irrespective of the solid support, and quantitative removal of AII from PAMR and MBHAR occurred in less than 3 h. However, about 10-15 h seemed to be necessary for cleavage of AII from BHAR, and in this extended cleavage reaction a significant increase in peptide degradation rate was observed. Regardless of the cleavage temperature used, the decreasing order of acid stability measured for resins was BHAR>MBHAR>PAMR. Collectively, these findings demonstrated the feasibility of applying TFMSA/TFA solution as a substitute for anhydrous HF at the cleavage step in Boc-SPPS methodology. Care should be taken however, as the cleavage efficacy depends on multiple factors including the resin, peptide sequence, the time and temperature of reaction.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Amino Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Indicators and Reagents,
http://linkedlifedata.com/resource/pubmed/chemical/Peptides,
http://linkedlifedata.com/resource/pubmed/chemical/Resins, Plant,
http://linkedlifedata.com/resource/pubmed/chemical/Solvents,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfides,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfonic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Trifluoroacetic Acid,
http://linkedlifedata.com/resource/pubmed/chemical/methylphenylsulfide
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
0009-2363
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
49
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1089-92
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:11558592-Amino Acids,
pubmed-meshheading:11558592-Chromatography, High Pressure Liquid,
pubmed-meshheading:11558592-Indicators and Reagents,
pubmed-meshheading:11558592-Mass Spectrometry,
pubmed-meshheading:11558592-Peptides,
pubmed-meshheading:11558592-Resins, Plant,
pubmed-meshheading:11558592-Solvents,
pubmed-meshheading:11558592-Sulfides,
pubmed-meshheading:11558592-Sulfonic Acids,
pubmed-meshheading:11558592-Trifluoroacetic Acid
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pubmed:year |
2001
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pubmed:articleTitle |
Evaluation of the trifluoromethanosulfonic acid/trifluoroacetic acid/thioanisole cleavage procedure for application in solid-phase peptide synthesis.
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pubmed:affiliation |
Department of Biophysics, Universidade Federal de São Paulo, SP, Brazil.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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