Aminoacyl‐Einlagerung. 1. Mitteilung. Definition, Übersicht und Beziehung zur Peptidsynthese

Abstract

zum 60. Geburtstag gewidrnet. (29.y. 57.) 1. Mitteilung. ~ ~~ , ) J . P. Zimmermann, Dissertation Universitat Basel, 1952. za) J . P. Zirnmermann, unveroffentlicht. 3, J . WehrmiiZZer, Dissertation Universitat Basel, 1955. 4, P. Quitt, Dissertation Universitat Basel, 1956. , ) Ob auch im Fall der Imidazolonbildung von AAE zu sprechen sei. ist rine Ermessensfrage. Wir werden bei spaterer Gelegenheit dirauf znriickkommen.

Total chemical synthesis of polypeptides and proteins: chemistry of ligation techniques and beyond

“…The foundation for such a type of technique was laid by Brenner et al more than 60 years ago. 130 Recently, Miranda et al reported the use of a 2-hydroxy-6-nitrobenzyl auxiliary with the intention of improving the efficiency and yield of peptide synthesis including the couplings involving sterically hindered amino acids. 131 Initially, through reductive alkylation, the auxiliary is attached to a resin-bound peptide.…”

Accessing posttranslationally modified proteins through thiol positioning

“…The described strategy holds the flexibility in synthesizing both N‐ and O‐linked glycopeptides/glycoproteins by suitably selecting the sugar substrate with appropriate functionality at the anomeric position and coupling it to side chain functionalities like hydroxyl (Thr, Ser) or carboxylates (Asn)17, 18. The flexibility of the ligation site revealed the importance of proximity effect as well as the significance of having primary amine in a similar fashion as revealed by studies on amine capture strategy for peptide bond formation through ON acyl transfer performed by Brenner et al ,22 Wieland et al ,23 and Kemp24. One important difference in NCL and SAL is the rate limiting step.…”

Synthesis Concepts for Peptides and Proteins

“…At the very beginning of chemical peptide synthesis Theodor Wieland [104] and Max Brenner [166] independently had the idea to convert the bimolecular reaction between two peptides to be ligated into an intramolecular reaction by bringing together the respective C-and N-termini on a template in order to facilitate intramolecular acyl transfer reaction. A similar mechanism is realized practically in the reverse ligase action of serine and cysteine proteases in which O-or S-acyl intermediates undergo an O-or S-to N-acyl transfer reaction forming a peptide bond.…”

“…The principle of a template-mediated amide bond formation according to Brenner et al [166] using a salicylamide template ( Figure 5.20) is based on a base-catalyzed intramolecular rearrangement [168]. Demonstrated in a general sense, the carboxy function of salicylic acid is acylated with an amino acid alkyl ester, whereas the hydroxy group is esterified with a protected amino acid.…”