Azapeptides

Gante, Joachim

doi:10.1055/s-1989-27269

Cited by 190 publications

(134 citation statements)

References 0 publications

Supporting

Mentioning

133

Contrasting

Order By: Relevance

“…The synthesis of azapeptides from substituted hydrazines or hydrazides can be carried out very easily. [38] When incorporating azaamino acid esters like compound 13 into a peptide chain azapep- Figure 5. Some of the more common modifications to the peptide backbone (adapted from literature [37] ).…”

Section: Azapeptidesmentioning

confidence: 99%

Peptidomimetics – A Versatile Route to Biologically Active Compounds

2009

View full text Add to dashboard Cite

Proteins are vital for basically every known organism. Therefore the investigation of their structure, the development of a deeper understanding of protein-protein interactions and the design of novel peptides, which selectively interact with proteins are fields of active research. Small peptides consisting of the 20 natural amino acids typically show high conformational flexibility and a low in-vivo stability which hampers their application as tools in medicinal diagnostics or molecular biology. One very versatile strategy to overcome such drawbacks is the use of peptidomimetics. These are small

show abstract

Section: Azapeptidesmentioning

confidence: 99%

Peptidomimetics – A Versatile Route to Biologically Active Compounds

2009

View full text Add to dashboard Cite

show abstract

“…1a-b Aza-peptides are peptide analogs that possess an azaamino acid residue in which the a-CH is replaced by a nitrogen atom (see Figure 1). 2 Aza-peptides have been shown to adopt b-turn conformers as predicted by computational analyses, [3][4][5] and observed by spectroscopic [5][6][7][8] and crystallographic 3-8 studies.…”

Section: Introductionmentioning

confidence: 99%

“…However, since the first synthesis of an aza-peptide (aza-Gly-aza-Gly-hydrazide by Stollé in 1910), the incorporation of aza-Gly in peptides has required challenging solution 2 and solid-supported chemistry, 18,19 which has often been plagued by poor yields and side reactions. The most commonly used method for incorporating aza-Gly into peptides has involved the addition of a carbazate 1 to either activated carbamate 3 or isocyanate 4 derived from the respective amino ester or amide 2 (see Figure 2).…”

mentioning

confidence: 99%

“…The most commonly used method for incorporating aza-Gly into peptides has involved the addition of a carbazate 1 to either activated carbamate 3 or isocyanate 4 derived from the respective amino ester or amide 2 (see Figure 2). 2 In competition with the synthesis of aza-Gly peptide 5, amino amidederived carbamates 3b and isocyanates 4b have been observed to form hydantoins 6, due to intramolecular amide acylation (see Figure 2). 20 Alternatively, activation of carbazate 1 has been used to couple the aza-Gly residue to amino esters or amino amides 2.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Benzophenone semicarbazone protection strategy for synthesis of aza‐glycine containing aza‐peptides

2008

View full text Add to dashboard Cite

Aza-glycine has been incorporated into peptide mimics as a tool for studying the active conformation and characterizing structure-function relationships for activity. Side reactions, such as intramolecular cyclizations to form hydantoins and oxadiazalones, have, however, inhibited efforts to make activated aza-Gly residues in solution using carbamate protection. Herein, we describe efficient incorporation of aza-glycine into aza-peptides using diphenyl hydrazone protection. Hydrazone acylation with p-nitrobenzyl chloroformate provided the protected aza-Gly activated ester, which was used to acylate a set of amino ester and amino acids to provide aza-Gly-Xaa aza-dipeptide fragments for peptide synthesis. Removal of the hydrazone protection was performed under acidic conditions to provide the hydrochloride salt of the aza-Gly residue for subsequent elongation of the aza-peptide chain using standard coupling conditions. A proof of concept for the use of benzophenone protection has been established by the synthesis of an aza-peptide analog of a potent activator of caspase 9 in cancer cells.

show abstract

“…These compounds are an interesting class of materials that have been used as building blocks in heterocyclic systems containing N-N bonds 2 and azapeptides 3 . Some hydrazines such as phthalazin-1-yl-hydrazine were widely used as a general antihypertensive, and vasodilator agents, some years ago and at the present time as a first-line drug in the management of pregnancy-induced hypertension 4,5 .…”

Section: Introductionmentioning

confidence: 99%