“Doubly Customizable” Unit for the Generation of Structural Diversity: From Pure Enantiomeric Amines to Peptide Derivatives

Readily available, low-cost 4R-hydroxy-l-proline (Hyp) is introduced as a “doubly customizable” unit for the generation of libraries of structurally diverse compounds. Hyp can be cleaved at two points, followed by the introduction of new functionalities. In the first cycle, the removal and replacement of the carboxylic group are carried out, followed (second cycle) by the scission of the 4,5-position and manipulation of the resulting chains. In this way, three new chains are generated and can be transformed independently to afford a diversity of products with tailored substituents, such as β-amino aldehydes, diamines, β-amino acid derivatives, including N-alkylated ones, or modified peptides. Many of these products are high-profit compounds but, in spite of their commercial value, are still scarce. Moreover, the process takes place with stereochemical control, and either pure R or S isomers can be obtained with small variations of the synthetic route.

Bibliographic Details

Main Authors:	Hernández, Dácil, Carro, Carmen, Boto, Alicia
Other Authors:	Interreg MAC
Format:	artículo biblioteca
Language:	English
Published:	American Chemical Society 2021-01-12
Subjects:	Lipids, Peptides and proteins, Equilibrium, Substitution reactions, Mixtures,
Online Access:	http://hdl.handle.net/10261/228393 http://dx.doi.org/10.13039/501100004837
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