Synthesis of a Naturally Occurring Diene‐Containing Amino Acid and Its Glutamyl Dipeptide via <i>N</i>‐Acyliminium Ion Chemistry

Berkheij, Martin; Dijkink, J.; David, Olivier; Sonke, Theo; IJzendoorn, Denis R.; Blaauw, Richard H.; Maarseveen, Jan H. van; Hiemstra, Henk

doi:10.1002/ejoc.200701016

Cited by 14 publications

(12 citation statements)

References 21 publications

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“…[170] The parent in this category, vinyl-Gly ( 42 , Figure 22A) is a known natural metabolite, [171] although its biosynthesis is not fully clear: a byproduct of PLP-containing γ-elimination enzymes would be one route. A related β,γ-olefinic amino acid is dehydro-Val ( 43 , Figure 22A), which occurs in the hexapeptide mycotoxin phomopsin A.…”

Section: Amino Acids With Potentially Reactive Functional Groupsmentioning

confidence: 99%

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

2013

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Freestanding nonproteinogenic amino acids have long been recognized for their antimetabolite properties and tendency to be uncovered to reactive functionalities by the catalytic action of target enzymes. By installing them regiospecifically into biogenic peptides and proteins, it may be possible to usher a new era at the interface between small molecule and large molecule medicinal chemistry. Site‐selective protein functionalization offers uniquely attractive strategies for posttranslational modification of proteins. Last, but not least, many of the amino acids not selected by nature for protein incorporation offer rich architectural possibilities in the context of ribosomally derived polypeptides. This Review summarizes the biosynthetic routes to and metabolic logic for the major classes of the noncanonical amino acid building blocks that end up in both nonribosomal peptide frameworks and in hybrid nonribosomal peptide‐polyketide scaffolds.

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Section: Amino Acids With Potentially Reactive Functional Groupsmentioning

confidence: 99%

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

2013

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“…Im Gegensatz dazu sind b,g-ungesättigte Aminosäuren stabil. [170] Die Stammverbindung dieser Kategorie, Vinyl-Gly (42, Abbildung 22 A) ist ein bekannter, natürlich vorkommender Metabolit, [171] dessen Biosynthese allerdings noch nicht vollständig aufgeklärt ist: ein Nebenprodukt von PLP-haltigen g-eliminierenden Enzymen wäre eine Mçglichkeit. Eine verwandte b,g-ungesättigte Aminosäure ist Dehydrovalin (43, Abbildung 22 A), das in dem hexapeptidischen Mycotoxin Phomopsin A vorkommt.…”

Section: Aminosäuren Mit Potenziell Reaktiven Funktionellen Gruppenunclassified

Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

2013

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Frei vorkommende nichtproteinogene Aminosäuren sind schon lange wegen ihrer antimetabolen Eigenschaften bekannt. Entdeckt werden sie meist aufgrund der Reaktivität gegenüber der katalytischen Wirkung der Zielenzyme. Führt man sie regiospezifisch in biogene Peptide und Proteine ein, kann es möglich werden, eine neue Ära der Medizinalchemie an der Grenze zwischen kleinen und großen Wirkstoffen einzuleiten. Außerdem eröffnet die ortsspezifische Funktionalisierung von Proteinen besonders attraktive Strategien für die posttranslationale Proteinmodifizierung. Auch bieten viele der Aminosäuren, die von der Natur nicht für den Einbau in Proteine ausgewählt wurden, reiche architektonische Möglichkeiten bei Einführung in ribosomal hergestellte Polypeptide. Dieser Aufsatz fasst die Biosynthesewege zu den wichtigsten Klassen nichtkanonischer Bausteine und deren Stoffwechsellogik zusammen, die in nichtribosomalen Peptidgerüsten und nichtribosomalen Peptid‐Polyketid‐Hybriden resultieren.

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“…Utilizing catalytic amounts of potassium t -butoxide led to the exclusive formation of tetrasubstituted tetrahydropyrans (THPs) 5 by a Michael addition, generating an additional stereogenic center diastereoselectively . Alternatively, DBU enables the selective formation of the α,β,γ,δ-unsaturated esters of type 6 mainly as the E , E -isomer (Scheme ) …”

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confidence: 99%

Multi-Component Regio- and Diastereoselective Cobalt-catalyzed Hydrovinylation/Allylboration Reaction Sequence

Erver

Hilt

2011

Org. Lett.

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The combination of a regioselective cobalt-catalyzed 1,4-hydrovinylation and the diastereoselective allylboronation reaction leads to a wide scope of functionalized hydroxydienyl esters in a one-pot reaction in excellent yields. With catalytic amounts of base, these products are easily converted either into α,β,γ,δ-unsaturated hydroxyl esters or complex tetrasubstituted tetrahydropyrans in chemo- and diastereoselective fashions. In addition, a high-yielding four-component one-pot reaction involving an acrylate, two different and unsymmetrical 1,3-dienes, and an unsaturated aldehyde is presented.

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Synthesis of a Naturally Occurring Diene‐Containing Amino Acid and Its Glutamyl Dipeptide via N‐Acyliminium Ion Chemistry

Cited by 14 publications

References 21 publications

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

Multi-Component Regio- and Diastereoselective Cobalt-catalyzed Hydrovinylation/Allylboration Reaction Sequence

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