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    Electronic Resource
    Electronic Resource
    Side Reaction with N-Carboxymethyl Amino Acids in the Synthesis of Backbone Cyclized Peptides (1998)
    Springer
    International journal of peptide research and therapeutics 5 (1998), S. 299-303 
    Details
    ISSN: 1573-3904
    Keywords: backbone cyclization ; bradykinin ; branched building units ; diketopiperazine formation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The use of N-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite the tert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of the N-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008806304435
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Side reaction withN-carboxymethyl amino acids in the synthesis of backbone cyclized peptides (1998)
    Springer
    International journal of peptide research and therapeutics 5 (1998), S. 299-303 
    Details
    ISSN: 1573-3904
    Keywords: backbone cyclization ; bradykinin ; branched building units ; diketopiperazine formation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary The use ofN-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite thetert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of theN-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02443547
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
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