Preparation of New α-Hydroxy Acids Derived from Amino Acids and Their Corresponding Polyesters

Cohen-Arazi, Naomi; Katzhendler, Jehoshua; Kolitz, Michal; Domb, Abraham J.

doi:10.1021/ma8012477

Cited by 48 publications

(48 citation statements)

References 15 publications

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“…[29] This procedure is stereoselective, with the S configuration of the standard proteinogenic amino acids (other than cysteine) being retained in the hydroxy acids. [29] This procedure is stereoselective, with the S configuration of the standard proteinogenic amino acids (other than cysteine) being retained in the hydroxy acids.…”

Section: Resultsmentioning

confidence: 99%

“…Ac ertain effect on yeast cell viability was seen by applyingt he pourplate method:t he number of colony-forming units (CFUs) after incubation with Mal-Ala (12 b)w as significantly highert han in the yeast blank and in the presence of all other (glycated) amino acids and peptides(Ta ble 2). This substancew as synthesized from pyrraline by the same methoda sa pplied for 14.P 2c oeluted with the standard substance 15 and fragmented in the same way.I tw as not possible to elucidate the stereospecificity of a-keto acid reduction.A lthough the S configurationo ft he amino acids is retained duringo ur synthesis procedure, [29,30] a-keto acid reductionb yd ifferent strains of Lactobacilli can lead to either the S or the R isomers. Therefore, mass and product ion spectra were recorded during chromatographic runs and compared with those of the yeast blank.…”

Section: Transformation Of Dipeptide-bound Glycated Amino Acidsmentioning

confidence: 99%

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Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

et al. 2016

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The yeast Saccharomyces cerevisiae transforms branched-chain and aromatic amino acids into higher alcohols in the Ehrlich pathway. During microbiological culturing and industrial fermentations, this yeast is confronted with amino acids modified by reducing sugars in the Maillard reaction (glycation). In order to gain some preliminary insight into the physiological "handling" of glycated amino acids by yeasts, individual Maillard reaction products (MRPs: fructosyllysine, carboxymethyllysine, pyrraline, formyline, maltosine, methylglyoxal-derived hydroimidazolone) were administered to two strains of S. cerevisiae in a rich medium. Only formyline was converted into the corresponding α-hydroxy acid, to a small extent (10 %). Dipeptide-bound pyrraline and maltosine were removed from the medium with concomitant emergence of several metabolites. Pyrraline was mainly converted into the corresponding Ehrlich alcohol (20-60 %) and maltosine into the corresponding α-hydroxy acid (40-60 %). Five specific metabolites of glycated amino acids were synthesized and characterized. We show for the first time that S. cerevisiae can use glycated amino acids as a nitrogen source and transform them into new metabolites, provided that the substances can be transported across the cell membrane.

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Section: Resultsmentioning

confidence: 99%

Section: Transformation Of Dipeptide-bound Glycated Amino Acidsmentioning

confidence: 99%

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

et al. 2016

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“…Scheme 1.6 shows a selection of such alternate polyester structures. Various amino acids were converted to the corresponding α -hydroxycarboxylic acid and then polymerized to give stereogenic α -substituted polyglycolide analogs [63,64] . This approach could give access to polymers with more tailored properties and sophisticated material properties.…”

Section: Alternate Systemsmentioning

confidence: 99%

Polyesters

Sisson

Schroeter

Lendlein

2011

Handbook of Biodegradable Polymers

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“…2,4 To overcome this limitation, syntheses of modified lactide monomers with functionalized side-chains have been reported in the past decade. 2,4–8 We have published the synthesis of cyclic lactides bearing protected alcohols, amines and carboxylic acid functionalities starting from commercially available amino acids. 9,10 Another versatile synthetic approach has been reported by Yang and coworkers who have synthesized functional hemilactides through a Passerini-type condensation.…”

Section: Introductionmentioning

confidence: 99%

Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains

et al. 2011

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Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloaddition between PEG-azides and a highly strained spirolactide-heptene monomer, which proceeds in high conversions. The PEG-grafted lactides analogues were polymerized via ring-opening polymerization using triazacyclodecene as organocatalyst to give well-defined tri- and hepta-(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG-poly(lactide) (PLA) with PEG chain Mn 2000 was also prepared but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3 E-1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

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Preparation of New α-Hydroxy Acids Derived from Amino Acids and Their Corresponding Polyesters

Cited by 48 publications

References 15 publications

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

Polyesters

Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains

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