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Publikationen - Natur- und Wirkstoffchemie

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Publikation

Wessjohann, L. A.; Kreye, O.; Rivera, D. G.; One-Pot Assembly of Amino Acid Bridged Hybrid Macromulticyclic Cages through Multiple Multicomponent Macrocyclizations Angew. Chem. 129, 3555-3559, (2017) DOI: 10.1002/ange.201610801

An important development in the field of macrocyclization strategies towards molecular cages is described. The approach comprises the utilization of a double Ugi four‐component macrocyclization for the assembly of macromulticycles with up to four different tethers, that is, hybrid cages. The innovation of this method rests on setting up the macromulticycle connectivities not through the tethers but through the bridgeheads, which in this case involve N‐substituted amino acids. Both dilution and metal‐template‐driven macrocyclization conditions were implemented with success, enabling the one‐pot formation of cryptands and cages including steroidal, polyether, heterocyclic, peptidic, and aryl tethers. This method demonstrates substantial complexity‐generating character and is suitable for applications in molecular recognition and catalysis.
Publikation

Wessjohann, L. A.; Kreye, O.; Rivera, D. G.; One-Pot Assembly of Amino Acid Bridged Hybrid Macromulticyclic Cages through Multiple Multicomponent Macrocyclizations Angew. Chem. Int. Ed. 56, 3501-3505, (2017) DOI: 10.1002/anie.201610801

An important development in the field of macrocyclization strategies towards molecular cages is described. The approach comprises the utilization of a double Ugi four‐component macrocyclization for the assembly of macromulticycles with up to four different tethers, that is, hybrid cages. The innovation of this method rests on setting up the macromulticycle connectivities not through the tethers but through the bridgeheads, which in this case involve N‐substituted amino acids. Both dilution and metal‐template‐driven macrocyclization conditions were implemented with success, enabling the one‐pot formation of cryptands and cages including steroidal, polyether, heterocyclic, peptidic, and aryl tethers. This method demonstrates substantial complexity‐generating character and is suitable for applications in molecular recognition and catalysis.
Publikation

Henze, M.; Kreye, O.; Brauch, S.; Nitsche, C.; Naumann, K.; Wessjohann, L. A.; Westermann, B.; Photoaffinity-Labeled Peptoids and Depsipeptides by Multicomponent Reactions Synthesis 2010, 2997-3003, (2010) DOI: 10.1055/s-0030-1258182

Photoaffinity tags can be incorporated easily into peptoids and congeners by the Ugi and Passerini multicomponent reactions. Products related to photo-methionine and photo-leucine can be accomplished by diazirine-containing building blocks. The same protocols can be used to synthesize derivatives with benzophenone photo cross-linkers.
Publikation

Rhoden, C. R. B.; Rivera, D. G.; Kreye, O.; Bauer, A. K.; Westermann, B.; Wessjohann, L. A.; Rapid Access to N-Substituted Diketopiperazines by One-Pot Ugi-4CR/Deprotection+Activation/Cyclization (UDAC) J. Comb. Chem. 11, 1078-1082, (2009) DOI: 10.1021/cc900106u

The most efficient diversity generating approaches to heterocycles are combinations of a multicomponent (MCR) with a cyclization reaction, for example, by Ugi-deprotection-cylization (UDC) protocols. If the desired post-Ugi reaction requires more than one deprotection, for example of two initially protected Ugi-reactive groups, or if it requires additional activation, for example, by an Ugi-activation-cyclization (UAC), either the isolation of intermediates or a sequential process or both become necessary. A recently introduced convertible isonitrile reagent allows a mild and chemoselective in situ post-Ugi activation of the isonitrile-born carboxylate with simultaneous deprotection of the nucleophilic amine, that is, liberation and activation of two Ugi-reactive groups, if desired also under subsequent lactam formation. This is exemplified by the synthesis of peptide-peptoid diketopiperazines.
Publikation

Westermann, B.; Michalik, D.; Schaks, A.; Kreye, O.; Wagner, C.; Merzweiler, K.; Wessjohann, L. A.; Natural Product Inspired meta/para’-Biaryl Ether Lactam Macrocycles by Double Ugi Multicomponent Reactions Heterocycles 73, 863-872, (2007) DOI: 10.3987/COM-07-S(U)21

Isonitrile meta/para’-functionalized biaryl ethers can serve as key building blocks for the highly efficient and diverse one step production of natural product inspired peptide/peptoid macrocycles, thereby forming up to 54-membered rings with eight or even sixteen new bonds. Aliphatic diamine and diacid tethers give access to two different classes of biaryl ether cyclopeptoids, either with exo/endo or exclusively endo dipeptidic moieties.
Publikation

Kreye, O.; Westermann, B.; Wessjohann, L.; A Stable, Convertible Isonitrile as a Formic Acid Carbanion [-COOH] Equivalent and Its Application in Multicomponent Reactions Synlett 2007, 3188-3192, (2007) DOI: 10.1055/s-2007-990912

The application of 2-(2,2-dimethoxyethyl) phenyl iso­nitrile in Ugi, Passerini, and Ugi-Smiles reactions is described. The simple transformation to highly activated indolyl amides allows functional-group conversion of the isonitrile moiety into a variety of carboxylic acid derivatives, overall acting as a neutral, nucleophilic COOH equivalent.
Publikation

Kreye, O.; Westermann, B.; Rivera, D.; Johnson, D.; Orru, R.; Wessjohann, L.; Dye-Modified and Photoswitchable Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) QSAR Comb. Sci. 25, 461-464, (2006) DOI: 10.1002/qsar.200540217

The m ultiple m ulticomponent m acrocyclization i ncluding b ifunctional b uilding b locks (MiB) strategy is suitable to obtain macrocycles with inherent dye or photoswitchable subunits. Provided as dicarboxylic components in Ugi‐MiBs, these functional subunits can be combined with natural like biarylether and peptoid moieties.
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