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Journal ArticleDOI

Activation of the amide group by acylation hydroxy- and aminoacyl incorporation in peptide systems.

01 Jan 1965-Tetrahedron (Pergamon)-Vol. 21, Iss: 12, pp 3537-3572
TL;DR: In this paper, a new reaction, the hydroxy-and aminoacyl incorporation in aliphatic and alicyclic N-hydrox-(amino)acl amides is described in detail.
About: This article is published in Tetrahedron.The article was published on 1965-01-01. It has received 72 citations till now. The article focuses on the topics: Amide & Cyclic peptide.
Citations
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Journal ArticleDOI
TL;DR: A convenient synthesis of 4-nitrobenzyl-substituted macrocyclic tetraamines and their conversion to bifunctional poly(amino carboxylate) chelating agents is described and preparation of the isothiocyanate derivatives and 14C labeled che lating agents are described.

116 citations

Journal ArticleDOI
TL;DR: This minireview has drawn on recent progress to highlight the key reaction design features that enable successful ‘normal-to-medium’ ring expansion for the synthesis of these medicinally important molecular frameworks.
Abstract: Medium-sized rings have much promise in medicinal chemistry, but are difficult to make using direct cyclisation methods. In this minireview, we highlight the value of ring expansion strategies to address this long-standing synthetic challenge. We have drawn on recent progress (post 2013) to highlight the key reaction design features that enable successful 'normal-to-medium' ring expansion for the synthesis of these medicinally important molecular frameworks, that are currently under-represented in compound screening collections and marketed drugs in view of their challenging syntheses.

94 citations

Book ChapterDOI
TL;DR: Hydrolysates of proteins and polypeptides often contain these anhydro-dimers of amino-acids and they are commonly isolated from cultures of yeast, lichens and fungi.
Abstract: Being relatively simple compounds, 2,5-dioxopiperazines are amongst the most ubiquitous peptide derivatives found in nature. Hydrolysates of proteins and polypeptides often contain these anhydro-dimers of amino-acids and they are commonly isolated from cultures of yeast, lichens and fungi. Their existence as a special group of compounds was first recognized around 1900 (1). The great Emil Fischer managed to synthesize many of the simpler members of this family in the early 1900’s (2). The parent compound, 2,5-dioxopiperazine, often referred to as cyclo-gly-gly*, was made in 1888 (3).

82 citations

References
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Journal ArticleDOI
TL;DR: In this paper, a neuer Umlagerungstypus beschrieben, welcher von O-aminoacylierten β-hydroxysaureamiden zu β-Hydroxyacyl-aminosaure amiden fuhrt.
Abstract: Unter dem Namen Aminoacyl-Einlagerung wird ein neuer Umlagerungstypus beschrieben, welcher von O-aminoacylierten β-Hydroxysaureamiden zu β-Hydroxyacyl-aminosaureamiden fuhrt. Die β-Hydroxysaure kann aliphatisch oder aromatisch sein. Da der Amidstickstoff substituiert sein darf, gestattet die Reaktion den Aufbau von Peptidketten. Peptide schienen bisher nur durch Aminoacyl-Anlagerungs-Reaktionen zuganglich zu sein. Die Aminoacyl-Einlagerungs-Reaktion weist einen prinzipiell neuen Weg.

49 citations

Journal ArticleDOI
TL;DR: The total synthesis of the Ergot alkaloid Ergotamine is described and the chiral stationary phase of the molecule is described.
Abstract: The total synthesis of the Ergot alkaloid Ergotamine is described.

43 citations