Synthesis of Peptides Related to Gramicidin S. II.<sup>1</sup> The Decapeptide Containing D-Tyrosine Residues in Place of D-Phenylalanine<sup>2</sup>

Erlanger, Bernard F.; Curran, William V.; Kokowsky, Nicholas

doi:10.1021/ja01538a029

Cited by 8 publications

References 2 publications

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Synthesis of Peptides with Mixed Anhydrides

Albertson

2011

Organic Reactions

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A mixed acid anhydride, or mixed anhydride, is a dehydration product of two polyoxy acids. For a mixed anhydride to be of interest for peptide synthesis, one of the components must, in general, be an alpha‐acylamino acid. The nature of the second component acid may vary widely. In this chapter the term mixed anhydride will be used in a more general sense. In addition to conventional mixed anhydrides, from polyoxyacids, reference will be made to “mixed anhydrides” otherwise recognizable as acyl halides, ethers, esters, thiol esters, O‐acylisoureas and isoimides. This chapter is limited to a review of chemistry of the acyclic alpha‐amino acid mixed anhydrides, which the well‐know alpha‐acylamino acid chlorides and azides, which have been the subject of an excellent review. In general, discussion of the application of alpha‐acyllamino acid mixed anhydrides will be limited to non‐polymeric peptide bond formation and will not be concerned with acylations other than those that lead to a peptide bonds.

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Synthesis of Peptides with Mixed Anhydrides

Albertson

2011

Organic Reactions

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Synthese einer geschützten Heptapeptidsequenz aus dem Tyrocidin B

Zahn

Brandenburg

1966

Justus Liebigs Ann. Chem.

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Carbobenzoxy-~-valyl-F-tosyl-~-ornithyl-~-leucyl-~-phenylalanyl-~-prolyl -L-tryptophyl-L-phenylalaninmethylester, ein Heptapeptidderivat mit einer der Tyrocidin-B-Sequenz 1-7 entsprechenden Aminosaurefolge, das L-Phenylalanin anstelle von D-Phenylatanin enthalt, sowie einige freie Teilpeptide wurden synthetisiert. Das homodet cyclische Peptid-Antibiotikum Tyrocidin B3) besitzt die Struktur4) : Val' -+ O m 2 -Leu3 + ~-P h e~ -* Pro5 c Tyr'O -Glug -Asp8 c D-Phe? -Try6 7 ~H Z I;J& Im Tyrocidin As) ist Try6 durch Phe, im Tyrocidin C6) jst ~-P h e 7 durch D-Try ersetzt. Gramjcidin S7) enthalt die Sequenz 1-5 zweimal.Lineare Gramicidin-S-Peptide wurden in verschiedenen Arbeitskreisen dargestelltg-ll). Die Synthese des cyclischen Dekapeptids sowie des Lysz-, Lys7-Analogon gelang Schwyzer und Sieberlz), die auch die Synthese eines geschiitzten Pentapeptids der Sequenz 6--10 von Tyrocidin A 13) beschrieben.

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