Chemoenzymatic synthesis of novel <i>N</i>
-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

Monsalve, Leandro N.; Petroselli, Gabriela; Erra-Ballsells, Rosa; Vázquez, Analı́a; Baldessari, Alicia

doi:10.1002/pi.4660

Cited by 7 publications

(2 citation statements)

References 40 publications

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“…Amid the wide variety of enzymes used in organic synthesis, lipases in non-aqueous media have an amazing promiscuity, being used for a broad range of reactions such as aminolysis, esterification, transesterification, polymerization, etc. [21][22][23][24][25]. In our laboratory several studies have been accomplished on the use of lipases, obtaining a wide variety of biologically active compounds, many of them new [26][27][28][29][30][31][32][33][34][35].…”

Section: Scheme 1 Structure Of Important Bile Acidsmentioning

confidence: 99%

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

et al. 2018

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In this work we present an efficient, environmentally friendly approach to the synthesis of a series of hyodeoxycholic acid derivatives applying Biocatalysis. Fifteen acetyl and ester derivatives, twelve of them new, were obtained through an enzymatic strategy in a fully regioselective way and in very good to excellent yield. In order to find the optimal reaction conditions, the influence of several parameters such as enzyme source, alcohol or acylating agent:substrate ratio, enzyme:substrate ratio, temperature and reaction solvent was considered. The excellent results obtained made this procedure very efficient, particularly considering the low amount of enzyme required. In addition, this methodology uses mild reaction conditions and has reduced environmental impact, making biocatalysis a suitable way to obtaining these bile acids derivatives.

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Section: Scheme 1 Structure Of Important Bile Acidsmentioning

confidence: 99%

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

et al. 2018

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“…Synthetic peptide analogues have been long sought after for their promising applications in biotechnology. , Poly(β-peptoid)s ( N -substituted poly-β-alanines) are a particularly intriguing class of pseudopeptidic polymers, which can formally be gained by the addition of a methylene unit in the backbone of polypeptoids or the N -substitution of poly(β-peptide)s. − Tertiary amides in a β-peptoid backbone offer higher proteolytic resistance and less polar as compared to typical peptide amide bonds. − Benefitting from a combination of biocompatibility, degradability, metabolic stability, and processability, β-peptoids have vast potential for therapeutic applications. , Furthermore, the extra C–C bond in the β-peptoid backbone would greatly expand the potential diversity of the peptoid shape as compared to α-peptoids. ,− In this regard, a great deal of effort has been made to develop poly(β-peptoid) materials with interesting structures for property investigation and biological applications in recent years. − …”

Section: Introductionmentioning

confidence: 99%

Oligo(β-peptoid)s with Backbone Chirality from Aspartic Acid Derivatives: Synthesis and Property Investigation

Huang

et al. 2020

ACS Omega

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Poly(β-peptoid)s (N-substituted poly-β-alanines) are an intriguing class of pseudopeptidic materials for biomedical applications, but the polymers prepared by solution polymerization have restricted diversity and functionality due to synthetic difficulty. Synthesis of structurally diverse poly(β-peptoid)s is highly desirable yet challenging. Herein, we report a new approach to synthesize skeletal chiral β-peptoid polymers from readily available aspartic acid derivatives. Two types of N-substituted β3-homoalanine monomers, i.e., N-(methyl propionate)-Asp-OMe ( N MeP-Asp-OMe) and N-(tert-butyl propionate)-Asp-OMe ( N tBuP-Asp-OMe), were synthesized in high yield via an aza-Michael addition reaction between l-aspartic acid-1-methyl ester (l-Asp-OMe) and acrylate species. Both N-substituted β3-homoalanines can be readily converted into polymerizable N-substituted β3-homoalanine N-carboxyanhydrides (β-NNCAs). Subsequent ring-opening polymerization (ROP) of these β-NNCA monomers provides access to oligo(β-peptoid)s and mPEG-poly(β-peptoid) diblocks with backbone chirality. Their conformations were preliminarily studied by circular dichroism (CD) spectra and Fourier transform infrared spectroscopy (FT-IR). The synthetic strategy would significantly facilitate the development of novel poly(β-peptoid)s with well-defined and diverse structures.

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Sequence Programmable Peptoid Polymers for Diverse Materials Applications

et al. 2015

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Polymer sequence programmability is required for the diverse structures and complex properties that are achieved by native biological polymers, but efforts towards controlling the sequence of synthetic polymers are, by comparison, still in their infancy. Traditional polymers provide robust and chemically diverse materials, but synthetic control over their monomer sequences is limited. The modular and step-wise synthesis of peptoid polymers, on the other hand, allows for precise control over the monomer sequences, affording opportunities for these chains to fold into well-defined nanostructures. Hundreds of different side chains have been incorporated into peptoid polymers using efficient reaction chemistry, allowing for a seemingly infinite variety of possible synthetically accessible polymer sequences. Combinatorial discovery techniques have allowed the identification of functional polymers within large libraries of peptoids, and newly developed theoretical modeling tools specifically adapted for peptoids enable the future design of polymers with desired functions. Work towards controlling the three-dimensional structure of peptoids, from the conformation of the amide bond to the formation of protein-like tertiary structure, has and will continue to enable the construction of tunable and innovative nanomaterials that bridge the gap between natural and synthetic polymers.

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Chemoenzymatic synthesis of novel N -(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

Cited by 7 publications

References 40 publications

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

Oligo(β-peptoid)s with Backbone Chirality from Aspartic Acid Derivatives: Synthesis and Property Investigation

Sequence Programmable Peptoid Polymers for Diverse Materials Applications

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