One-pot oligoamides syntheses from<scp>l</scp>-lysine and<scp>l</scp>-tartaric acid

Oliva, Rosangela; Ortenzi, Marco Aldo; Salvini, Antonella; Papacchini, Alessandra; Giomi, Donatella

doi:10.1039/c7ra00676d

Cited by 11 publications

(10 citation statements)

References 42 publications

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“…This process gives the formation of oligoamides via one-step growth polycondensation of L-lysine in the presence of boric acid by thermal treatment at 240°C. 46 1 H NMR (Fig. S1-S4 †) well support the formation of a hyperbranched polylysine structure (Fig.…”

Section: Resultssupporting

confidence: 55%

Effective SARS-CoV-2 antiviral activity of hyperbranched polylysine nanopolymers

et al. 2021

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Section: Resultssupporting

confidence: 55%

Effective SARS-CoV-2 antiviral activity of hyperbranched polylysine nanopolymers

et al. 2021

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“…Furthermore, stereochemistry has not been directly invoked in order to modulate properties in most of these examples. Synthetic polyamides possessing chiral centres are comparatively abundant and well represented in the literature with the stereochemistry usually derived from the use of naturally occurring comonomers and/or precursors, such as sugars [40][41][42][43][44][45][46][47][48] , amino acids 49,50 , tartaric acid [51][52][53] and terpenes [54][55][56] . A central feature among the stereo-defined polyamides is their inherent crystallinity, which has been assessed in most instances.…”

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confidence: 99%

Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

Worch

Weems

et al. 2020

Nat Commun

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Biocompatible polymers are widely used in tissue engineering and biomedical device applications. However, few biomaterials are suitable for use as long-term implants and these examples usually possess limited property scope, can be difficult to process, and are nonresponsive to external stimuli. Here, we report a class of easily processable polyamides with stereocontrolled mechanical properties and high-fidelity shape memory behaviour. We synthesise these materials using the efficient nucleophilic thiol-yne reaction between a dipropiolamide and dithiol to yield an α,β − unsaturated carbonyl moiety along the polymer backbone. By rationally exploiting reaction conditions, the alkene stereochemistry is modulated between 35-82% cis content and the stereochemistry dictates the bulk material properties such as tensile strength, modulus, and glass transition. Further access to materials possessing a broader range of thermal and mechanical properties is accomplished by polymerising a variety of commercially available dithiols with the dipropiolamide monomer.

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“…As the basic building blocks of proteins, natural amino acids widely exist in various organisms. At present, since various natural amino acids and their derivatives can be produced on an industrial scale under the existing technical conditions, they have been used as sustainable raw materials to prepare bio‐based polymers 21–25 . Benzoxazines derived from natural amino acids have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Bio‐basedbenzoxazine from renewableL‐tyrosine: Synthesis, polymerization, and properties

Ren

Tian

Zhang

et al. 2022

Journal of Polymer Science

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Developing thermosets derived from renewable sources is of great importance. In this work, a fully bio-based benzoxazine monomer, 3,6-bis ((3-(furan-2-ylmethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)methyl)piperazine-2,5-dione (TCDPF), is conveniently synthesized from L-tyrosine cyclic dipeptide (TCDP), furfurylamine and paraformaldehyde. The chemical structure of TCDPF is confirmed by nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy (FT-IR) techniques. The curing behavior of TCDPF is investigated by differential scanning calorimetry and in situ FT-IR techniques. After temperatureprogrammed curing, the thermomechanical property and thermal stability of the resulting TCDPF polymer (PTCDPF) are evaluated by dynamic mechanical analysis and thermogravimetric analysis techniques, respectively. It is found that PTCDPF have excellent comprehensive performance such as high glass transition temperature (T g = 322 C), high thermal degradation temperature (T 5% = 342 C, T 10% = 395 C in N 2 atmosphere), and high char yield (CY = 51.3% at 800 C in N 2 atmosphere). The results demonstrate that L-tyrosine is a promising bio-based raw material for preparing high performance polybenzoxazines.

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One-pot oligoamides syntheses froml-lysine andl-tartaric acid

Abstract: Oligoamides based on natural raw materials, l-lysine and l-tartaric acid, were synthesized using one-pot processes. A l-lysine diketopiperazine structure was obtained with good selectivity without protection/deprotection steps.

Cited by 11 publications

References 42 publications

Effective SARS-CoV-2 antiviral activity of hyperbranched polylysine nanopolymers

Effective SARS-CoV-2 antiviral activity of hyperbranched polylysine nanopolymers

Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

Bio‐basedbenzoxazine from renewableL‐tyrosine: Synthesis, polymerization, and properties

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