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Journal ArticleDOI

Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1‐Hydroxy‐benzotriazolen

01 Mar 1970-Chemische Berichte (John Wiley & Sons, Ltd)-Vol. 103, Iss: 3, pp 788-798
TL;DR: In this article, the authors show that 1-Hydroxy-benzotriazol and 1-hydroxy-acetyl carbodiimid-methode eignen sich als Zusatze bei der Dicyclohexylcarbodiimids-Methode zur Synthese von Peptiden, verhindern die N-Acyl-harnstoffbildung and fuhren in hoher Ausbeute.
Abstract: 1-Hydroxy-benzotriazol sowie verschiedene kernsubstituierte 1-Hydroxy-benzotriazole eignen sich als Zusatze bei der Dicyclohexylcarbodiimid-Methode zur Synthese von Peptiden. Ihr Einflus auf die Racemisierung bei Peptidsynthesen wurde unter Anwendung des gaschromatographischen Racemisierungstests von Weygand u. Mitarbb.2) untersucht. Die neuen Zusatze senken die Racemisierung, verhindern die N-Acyl-harnstoffbildung und fuhren in hoher Ausbeute zu sehr reinen Peptiden.
Citations
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Journal ArticleDOI
TL;DR: The great variety of conditions under which Fmoc solid phase peptide synthesis may be carried out represents a truly "orthogonal" scheme, and thus offers many unique opportunities for bioorganic chemistry.
Abstract: 9-Fluorenylmethoxycarbonyl (Fmoc) amino acids were first used for solid phase peptide synthesis a little more than a decade ago. Since that time, Fmoc solid phase peptide synthesis methodology has been greatly enhanced by the introduction of a variety of solid supports, linkages, and side chain protecting groups, as well as by increased understanding of solvation conditions. These advances have led to many impressive syntheses, such as those of biologically active and isotopically labeled peptides and small proteins. The great variety of conditions under which Fmoc solid phase peptide synthesis may be carried out represents a truly "orthogonal" scheme, and thus offers many unique opportunities for bioorganic chemistry.

2,336 citations

Journal ArticleDOI
TL;DR: This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of "acronym" based reagents.
Abstract: Amide bond formation is a fundamentally important reaction in organic synthesis, and is typically mediated by one of a myriad of so-called coupling reagents. This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of “acronym” based reagents. It aims to demystify the process allowing the chemist to make a sensible and educated choice when carrying out an amide coupling reaction (179 references).

1,686 citations

Journal ArticleDOI
TL;DR: A method is suggested for the synthesis of multicomponent peptide mixtures with main point of modification that before every coupling cycle the resin is divided into equal parts and each portion is coupled with a different amino acid.
Abstract: A method is suggested for the synthesis of multicomponent peptide mixtures. The method is a solid phase synthesis modified in order to give a closely equimolar mixture of peptides with predetermined sequences. The main point of modification is that before every coupling cycle the resin is divided into equal parts and each portion is coupled with a different amino acid. Then the portions are mixed and before the next coupling cycle the resin is again distributed into equal portions. The method is illustrated by the synthesis of a mixture of 27 tetrapeptides and that of 180 pentapeptides.

1,101 citations

Journal ArticleDOI
TL;DR: A general synthetic procedure for new derivatives of different N-hydroxy compounds has been developed and these either act as excellent activating reagents causing low racemization during condensation of peptide segments or are useful tools for the formation of active esters suitable for couplings in mixed aqueous / organic media, respectively.

950 citations

Journal ArticleDOI
09 May 1997-Science
TL;DR: The compound N -(17-hydroxylinolenoyl)-l-glutamine (named here volicitin) was isolated from oral secretions of beet armyworm caterpillars and induced the seedlings to emit volatile compounds that attract parasitic wasps and natural enemies of the herbivores.
Abstract: The compound N -(17-hydroxylinolenoyl)-l-glutamine (named here volicitin) was isolated from oral secretions of beet armyworm caterpillars. When applied to damaged leaves of corn seedlings, volicitin induces the seedlings to emit volatile compounds that attract parasitic wasps, natural enemies of the caterpillars. Mechanical damage of the leaves, without application of this compound, did not trigger release of the same blend of volatiles. Volicitin is a key component in a chain of chemical signals and biochemical processes that regulate tritrophic interactions among plants, insect herbivores, and natural enemies of the herbivores.

927 citations

References
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Journal ArticleDOI
TL;DR: In this paper, the geschutzte Teilsequenz 22-29 des Glucagons, wird auf zwei verschiedenen Wegen synthetisiert.
Abstract: N-Phthalyl-L-phenylalanyl-L-valyl-L-glutaminyl-L-tryptophyl-L-leucyl-L-methionyl-L-asparaginyl-O-tert.-butyl-L-threonin-tert.-butylester, die geschutzte Teilsequenz 22–29 des Glucagons, wird auf zwei verschiedenen Wegen synthetisiert.

163 citations