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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
6
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pubmed:dateCreated |
2008-3-17
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pubmed:abstractText |
beta-Hydroxy acids were reacted with hexafluoroacetone and carbodiimides to give carboxy-activated six-membered lactones in good yields. On reaction with amines, the corresponding amides were obtained. We demonstrate the following applications of this protecting/activating strategy: preparation of carboxamides in solution and on solid phase (both normal and reverse mode); recovery and reuse of the excess material in solid-phase synthesis; and convergent solid-phase peptide synthesis (CSPPS) with peptide segments bearing C-terminal Ser or Thr with very low levels of epimerization (<1%, HPLC).
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Acetone,
http://linkedlifedata.com/resource/pubmed/chemical/Amides,
http://linkedlifedata.com/resource/pubmed/chemical/Amino Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Carbodiimides,
http://linkedlifedata.com/resource/pubmed/chemical/Fluorenes,
http://linkedlifedata.com/resource/pubmed/chemical/Fluorocarbons,
http://linkedlifedata.com/resource/pubmed/chemical/Hydroxy Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Lactones,
http://linkedlifedata.com/resource/pubmed/chemical/Malates,
http://linkedlifedata.com/resource/pubmed/chemical/N(alpha)-fluorenylmethyloxycarbonyla...,
http://linkedlifedata.com/resource/pubmed/chemical/Peptides,
http://linkedlifedata.com/resource/pubmed/chemical/hexafluoroacetone,
http://linkedlifedata.com/resource/pubmed/chemical/malic acid
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0022-3263
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
21
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pubmed:volume |
73
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
2311-4
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pubmed:meshHeading |
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pubmed:year |
2008
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pubmed:articleTitle |
A novel protecting/activating strategy for beta-hydroxy acids and its use in convergent peptide synthesis.
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pubmed:affiliation |
Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1-5, E-08028 Barcelona, Spain. jan.spengler@irbbarcelona.com
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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