Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: a side reaction in peptide synthesis

Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: a side reaction in peptide synthesis

Formation of by‐products pyroglutamylglutamine diketopiperazine (5a) or pyroglutamylasparagine diketopiperazine (5b) were observed during the condensation of pyroglutamic acid active ester with C‐protected glutaminyl(or asparaginyl)‐proline derivatives. Successful synthesis of Glp‐Gln(or Asn)‐Pro‐de...

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Veröffentlicht in:International Journal of Peptide and Protein Research 1993-07, Vol.42 (1), p.14-19
Hauptverfasser: MAZUROV, ANATOLY A., ANDRONATI, SERGEI A., KOROTENKO, TAMARA I., GORBATYUK, VITALY YA, SHAPIRO, YURY E.
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acid Sequence
asparagine
Chemistry
diketopiperazine
Evaluation Studies as Topic
Exact sciences and technology
glutamine
Magnetic Resonance Spectroscopy
Methods
Molecular Sequence Data
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Organic chemistry
Peptides
Peptides, Cyclic - chemical synthesis
Piperazines - chemical synthesis
Preparations and properties
pyroglutamic acid
Pyrrolidonecarboxylic Acid - analogs & derivatives
side-reaction
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Zusammenfassung:Formation of by‐products pyroglutamylglutamine diketopiperazine (5a) or pyroglutamylasparagine diketopiperazine (5b) were observed during the condensation of pyroglutamic acid active ester with C‐protected glutaminyl(or asparaginyl)‐proline derivatives. Successful synthesis of Glp‐Gln(or Asn)‐Pro‐derivatives is possible after coupling of Glp‐Gln(or Asn)‐OH with proline‐derivatives.
ISSN:0367-8377
1399-3011
DOI:10.1111/j.1399-3011.1993.tb00343.x