Spätphasenfunktionalisierung von Peptiden und Cyclopeptiden mithilfe von Organozinkreagenzien

Leroux, Marcel; Vorherr, Thomas; Lewis, Ian; Schaefer, Michael; Koch, Guido; Karaghiosoff, Konstantin; Knöchel, Paul

doi:10.1002/ange.201902454

Cited by 7 publications

(1 citation statement)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The growing interest in chemically modified peptides due to their therapeutic potential triggered efforts to develop efficient and versatile strategies to achieve late‐stage functionalization (LSF) [25–27] . LSF represents a more convergent approach to modify peptides with respect to the introduction during solid‐phase peptide synthesis (SPPS) of UAAs which must be prepared and isolated as needed, often in a time and resource‐consuming manner.…”

Section: Late‐stage Functionalization Of Peptidesmentioning

confidence: 99%

Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides

2023

View full text Add to dashboard Cite

Peptide drug discovery often benefits from the large structural diversity permitted by unnatural amino acids (UAAs). Indeed, numerous approved peptide drugs include UAAs in their sequences. Therefore, innovative chemical approaches either to synthesize UAAs or to allow late‐stage functionalization of peptides are emerging themes in peptide drug discovery. Thanks to the recent advances in deaminative strategies using alkylpyridiniums salts, often referred to as Katritzky salts, a variety of radical alkylation methods have been developed. In recent years the use of Katritzky salts have become popular in peptide chemistry due to their ease of preparation from a primary amine, which is a predominant functional group in amino acids. This review highlights the progress that has been made by using Katritzky salts in the synthesis of UAAs, late‐stage peptide functionalization, and peptide macrocyclization.

show abstract

Section: Late‐stage Functionalization Of Peptidesmentioning

confidence: 99%

Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides

2023

View full text Add to dashboard Cite

show abstract

ppm Pd‐Containing Nanoparticles as Catalysts for Negishi Couplings … in Water

Wong

Lipshutz

2022

Angewandte Chemie

View full text Add to dashboard Cite

New technology is reported that enables Negishi couplings to be run under sustainable, far greener conditions. Thus, ppm Pd‐containing nanoparticles (NPs) have been developed that catalyze couplings in recyclable water under very mild conditions. These heterogeneous reactions involve loadings of Pd of typically only 2500 ppm (0.25 mol %). Highly functionalized aromatic and heteroaromatic bromides readily participate, including examples taken from the Merck Informer Library indicative of the functional group tolerance associated with these couplings. Direct comparisons with existing literature routes are made. Very low residual levels of Pd in newly formed products are to be expected, as determined by ICP‐MS. The reagent involved has been extensively characterized via DLS, TEM, cryo‐TEM, and EDX measurements.

show abstract

Late‐Stage Formal Double C−H Oxidation of Prenylated Molecules to Alkylidene Oxetanes and Azetidines by Strain‐Enabled Cross‐Metathesis

et al. 2023

View full text Add to dashboard Cite

Prenylation is a ubiquitous late‐stage modification in nature that often confers significantly improved bioactivity for secondary metabolites. While this lipophilic modification renders enhanced potency, the lipophilic tag(s) can diminish bioavailability and adversely alter drug transportation and metabolism. Thus, a functional‐group‐tolerant, mild, and selective late‐stage C−H functionalization of prenyl tags would present a great potential in drug discovery programs but could also impact other fields, such as agrochemistry and chemical biology. Herein we report an exocyclic‐strain‐driven cross‐metathesis reaction of prenyl tags, a formal double C−H oxidation protocol, that can be used for the selective late‐stage derivatization of prenylated compounds and natural products. This methodology avoids the need for prefunctionalization of target molecules and affords ready access to an unprecedented library of oxo‐ and aza‐prenylated complex molecules. Thus, in a broader context, this methodology extends late‐stage functionalization beyond that available to nature.

show abstract

Spätphasenfunktionalisierung von Peptiden und Cyclopeptiden mithilfe von Organozinkreagenzien

Cited by 7 publications

References 67 publications

Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides

Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides

ppm Pd‐Containing Nanoparticles as Catalysts for Negishi Couplings … in Water

Late‐Stage Formal Double C−H Oxidation of Prenylated Molecules to Alkylidene Oxetanes and Azetidines by Strain‐Enabled Cross‐Metathesis

Contact Info

Product

Resources

About