<scp>l</scp>-Dopa in small peptides: an amazing functionality to form supramolecular materials

Giuri, Demetra; Ravarino, Paolo; Tomasini, Claudia

doi:10.1039/d1ob00378j

Cited by 17 publications

(15 citation statements)

References 58 publications

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“…For this aim, we prepared some gels using Boc-L-DOPA(Bn) 2 -OH [ 45 , 46 ], a gelator widely used in our research lab ( Figure 2 ) [ 47 ]. This gelator can form a variety of noncovalent interactions (π-π stackings between the aromatic rings and H-bonds in the carbamate and carboxylic acid portions, as illustrated in Figure S1 ) and demonstrated its robustness forming gels under several conditions and in the presence of different fillers [ 10 , 48 , 49 , 50 ].…”

Section: Resultsmentioning

confidence: 99%

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Cenciarelli

Falini

Giuri

et al. 2023

Gels

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Fragrances are volatile organic compounds widely used in our daily life. Unfortunately, the high volatility required to reach human receptors reduces their persistency in the air. To contrast this effect, several strategies may be used. Among them, we present here the combination of two techniques: the microencapsulation in supramolecular gels and the use of profragrances. We report a study on the controlled lactonization of four esters derived from o-coumaric acid. The ester lactonization spontaneously occurs after exposure to solar light, releasing coumarin and the corresponding alcohol. To determine the rate of fragrance release, we compared the reaction in solution and in a supramolecular gel and we demonstrated that the lactonization reaction always occurs slower in the gel. We also studied the more suitable gel for this aim, by comparing the properties of two supramolecular gels obtained with the gelator Boc-L-DOPA(Bn)2-OH in a 1:1 ethanol/water mixture in different gelator concentration (0.2% and 1% w/v). The gel prepared with 1% w/v gelator concentration is stronger and less transparent than the other and was used for the profragrances encapsulation. In any case, we obtained a significative reduction of lactonization reaction in gel, compared with the same reaction in solution.

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Section: Resultsmentioning

confidence: 99%

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Cenciarelli

Falini

Giuri

et al. 2023

Gels

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“…66 L-DOPA is another aromatic amino acid that has gained wide attention for its bioactivity, and inclusion into self-assembled nanostructures, as recently reviewed by Tomasini's group. 67 However, when Phe was substituted with L-DOPA in the dipeptides DOPA-DOPA, nanofibrillar soft materials were obtained, with no evidence for nanotubes with a distinct inner cavity. 68…”

Section: L-dipeptides Without Derivatisationsmentioning

confidence: 99%

Nanotubes and water-channels from self-assembling dipeptides

2023

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“…Owing to the high versatility, good biocompatibility, and broad adhesion behavior DOPA-functionalization of polymers has become the gold standard for improving their adhesion properties. Indeed, numerous studies on l -DOPA-modified polymers (and smaller molecules) are available in the literature [ [194] , [195] , [196] , [197] ]. In most cases, this DOPA-modification conveys adhesive properties to the conjugate without interfering with other molecular characteristics of the target molecule.…”

Section: Chemistry Of Biological Adhesives and Their Biomedical Applicationsmentioning

confidence: 99%

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

Lutz

Kımna

Casini

et al. 2022

Materials Today Bio

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With the “many-headed” slime mold Physarum polycelphalum having been voted the unicellular organism of the year 2021 by the German Society of Protozoology, we are reminded that a large part of nature's huge variety of life forms is easily overlooked – both by the general public and researchers alike. Indeed, whereas several animals such as mussels or spiders have already inspired many scientists to create novel materials with glue-like properties, there is much more to discover in the flora and fauna. Here, we provide an overview of naturally occurring slimy substances with adhesive properties and categorize them in terms of the main chemical motifs that convey their stickiness, i.e. , carbohydrate-, protein-, and glycoprotein-based biological glues. Furthermore, we highlight selected recent developments in the area of material design and functionalization that aim at making use of such biological compounds for novel applications in medicine – either by conjugating adhesive motifs found in nature to biological or synthetic macromolecules or by synthetically creating (multi-)functional materials, which combine adhesive properties with additional, problem-specific (and sometimes tunable) features.

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l-Dopa in small peptides: an amazing functionality to form supramolecular materials

Abstract: L-Dopa (3,4-dihydroxyphenylalanine) is a chiral amino acid generated via biosynthesis from L-tyrosine in plants and some animals. The presence of multiple interacting sites makes L-Dopa a multifunctional building block for...

Cited by 17 publications

References 58 publications

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Nanotubes and water-channels from self-assembling dipeptides

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

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