D proline

Manufactured by Merck Group

Sourced in United States

D-proline is a laboratory reagent used in various biochemical and analytical applications. It is an amino acid isomer that serves as a building block for protein synthesis and other biomolecular processes. D-proline can be utilized in various research and testing procedures, though its specific applications and intended use should be determined by the user.

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Proline

9 protocols using d proline

Dietary Sugar Modulation of Drosophila Development

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Cultures were carried out on a modified Bloomington semi-defined medium (https://bdsc.indiana.edu/information/recipes/germanfood.html), containing Sucrose (0.15 and 1.0 M in CD and HSD, respectively) as the only purified sugar source. Ingredients were obtained from; Agar (Fisher Scientific; BP2641-1), Brewer’s Yeast (MP Biomedicals; 903312, Lot: BCBN0171V), Yeast Extract (Sigma-Aldrich; 70161), Peptone (Sigma-Aldrich; 82303), Sucrose (Fisher Scientific; S/8560/63), Magnesium sulfate hexahydrate (Fluka; 00627), Calcium chloride dihydrate (Sigma-Aldrich; 223506), Propionic acid (Sigma-Aldrich; P1386), p-Hydroxy-benzoic acid methyl ester (Sigma-Aldrich; H5501). For dietary supplementation experiments, L-proline (Sigma-Aldrich; P5607), D-proline (Sigma-Aldrich; 858919), L-glycine (VWR Chemicals; 101196X), L-alanine (Sigma-Aldrich; 7627), L-tryptophan (Sigma-Aldrich; T0254), Indole-5-carboxylic acid (Sigma-Aldrich; I5400) and IPA (Sigma-Aldrich; 57400) were added to CD or HSD. Cultures were performed at 25 °C unless otherwise noted. HSD feeding led to a developmental delay in reaching the third-instar larval stage; all experiments were performed on late third-instar larvae at day 8 after egg laying (CD) and day 14 after egg laying (HSD) unless otherwise noted.

Newton H., Wang Y.F., Camplese L., Mokochinski J.B., Kramer H.B., Brown A.E., Fets L, & Hirabayashi S. (2020). Systemic muscle wasting and coordinated tumour response drive tumourigenesis. Nature Communications, 11, 4653.

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Amino Acid Synthesis and Characterization

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d-Alanine, d-Arginine, d-Asparticacid, d-Asparagine, d-Glutamicacid, d-Histidine, d-Isoleucine, d-Leucine, d-Lysine, d-Methionine, d-Phenylalanine, d-Proline, d-Serine, d-Threonine, d-Tryptophan, d-Tyrosine, d-Valine, KBr (spectral grade), bovine serum albumin (BSA), glutathione and 3,3′,5,5′-tetramethylbenzidine (TMB) were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). d-Cystine and d-Glutarnine were purchased from Aladdin Reagent Co, Ltd. (Shanghai, China). All other chemicals and reagents were of analytical grade. All aqueous solutions were prepared with Milli-Q water.

Jiang N., Zhang C., Li M., Li S., Hao Z., Li Z., Wu Z, & Li C. (2021). The Fabrication of Amino Acid Incorporated Nanoflowers with Intrinsic Peroxidase-like Activity and Its Application for Efficiently Determining Glutathione with TMB Radical Cation as Indicator. Micromachines, 12(9), 1099.

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Synthesis and Characterization of Zinc Prolinate

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L-lactide (Purac Biochem, Gorinchem, the Netherlands) was purified by recrystallization from dried ethyl acetate (over calcium hydride) before use and thoroughly dried for 24 hours under vacuum at 30°C. Ciprofloxacin, L-proline, D-proline, and zinc acetate were supplied by Sigma-Aldrich, (St Louis, MO, USA). Zinc prolinate (L- and/or D-) was prepared from zinc acetate and L- and/or D-proline33 (link) and dried to a constant weight before use. 1-dodecanol and glycerol were distilled under reduced pressure. Pentaerythritol was purified by sublimation under reduced pressure. All other chemicals and solvents were analytical-grade from SD Fine (Mumbai, India) and were used without further purification. Double-distilled water was used in all experiments.

Parwe S.P., Chaudhari P.N., Mohite K.K., Selukar B.S., Nande S.S, & Garnaik B. (2014). Synthesis of ciprofloxacin-conjugated poly (L-lactic acid) polymer for nanofiber fabrication and antibacterial evaluation. International Journal of Nanomedicine, 9, 1463-1477.

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Amino Acid Supplementation Protocol

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l-Proline (purity >98.5%), d-proline (purity ≥99%) and l-alanine (purity >98.5%) were obtained from Sigma-Aldrich. Solutions were made by dissolving additives in culture media (details of culture media below). All amino acid solutions were sterile filtered with 0.2 μm syringe filters before application to cells. Filters were obtained from Fisher.

Murray A., Kilbride P, & Gibson M.I. (2023). Proline pre-conditioning of Jurkat cells improves recovery after cryopreservation. RSC Medicinal Chemistry, 14(9), 1704-1711.

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Proline Concentration Effect on FTIR Spectra

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Aqueous 100 mM ammonium acetate solutions of L-proline and D-proline (Sigma-Aldrich, St. Louis, MO, USA) were prepared such that the proline concentration varied by a factor of ~10⁵. Racemic solutions were prepared from aliquots of standard solutions containing the different enantiomers. For the FTIR studies, samples were dried to remove all H₂O and samples were reconstituted in 100 mM ammonium acetate in deuterium oxide (D₂O) to the desired proline concentrations.

Jacobs A.D., Jose K.V., Horness R., Raghavachari K., Thielges M.C, & Clemmer D.E. (2017). Cooperative Formation of Icosahedral Proline Clusters from Dimers. Journal of the American Society for Mass Spectrometry, 29(1), 95-102.

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Quantitative Proline Determination in Leaf Samples

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Proline content was determined according to Bates et al. (1973) (link). Briefly, 200 mg of leaf samples were ground using liquid nitrogen and homogenized in 3% sulfosalicylic acid followed by centrifugation at 12,000 g for 10 min. One ml of homogenate was taken and mixed with 1 ml of acid-ninhydrin and 1 ml of glacial acetic acid in a test tube for 1 h in a water bath at 100°C and then kept on ice to terminate the reaction. Then, 2 ml toluene was added to the reaction mixture with vigorous mixing and left at room temperature for 30 min until the separation of the two phases. The optical density of the chromophore-containing toluene (upper phase) was measured spectrophotometrically at 520 nm. The proline concentration was determined from a standard curve using D-Proline (Sigma-Aldrich, U.S.A.).

Shreya S., Supriya L, & Padmaja G. (2022). Melatonin induces drought tolerance by modulating lipoxygenase expression, redox homeostasis and photosynthetic efficiency in Arachis hypogaea L. Frontiers in Plant Science, 13, 1069143.

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Cytotoxic Metal Complexes: Synthesis and Evaluation

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All solvents were of analytical grade and used without further purification (except the solutions used for the DNA cleavage assay, vide infra). [RhCp*(μ-Cl)Cl]₂, [Ru(η⁶-p-cymene)(μ-Cl)Cl]₂, 5-chloro-8-hydroxyquinoline, D-proline, D-homoproline, aqueous formaldehyde (30% (v/v)), pic, phen, KNO₃, HNO₃, KOH, n-octanol, CD₃OD, D₂O, doxorubicin, EB, HSA (A8763, essentially globulin free), ct-DNA, DG, 4,4-dimethyl-4-silapentane-1-sulfonic acid (DSS) were Sigma-Aldrich (St. Louis, MO, USA) products and were used without further purification. FHA was purchased from GenScript (Piscataway, NJ, USA). NaH₂PO₄, Na₂HPO₄, KH₂PO₄, KCl, NaCl, diethyl-ether, n-hexane, ethanol, ethyl acetate and methanol were purchased from Molar Chemicals (Halásztelek, Hungary) or Reanal (Budapest, Hungary). [RuCym(HQCl-L-Pro)Cl]Cl and [RhCp*(HQCl-L-Pro)Cl]Cl were used in some cases due to comparative reasons, and their preparation and characterization were reported in our previous work [25 (link)].

Pivarcsik T., Dömötör O., Mészáros J.P., May N.V., Spengler G., Csuvik O., Szatmári I, & Enyedy É.A. (2021). 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules. International Journal of Molecular Sciences, 22(20), 11281.

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Preparation of Amino Acid Solutions

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D-methionine, D-tryptophan, D-leucine, D- or L-cysteine, D- or L-aspartic acid, D- or L-glutamic acid, D-alanine, D-threonine, D-valine, D-isoleucine, D-glutamine, D-phenylalanine, D-histidine, D-proline, D-lysine, D-arginine, and glycine (Sigma-Aldrich, St. Louis, MO, USA) were all prepared at a concentration of 40 mM, and D-tyrosine was prepared at a concentration of 0.8 mM due to its low solubility. Nisin powder (2.5% purity, Sigma-Aldrich, St. Louis, MO, USA) was dissolved in a solution at pH 2 to obtain a stock solution with a concentration of 1 g/L.

Tong Z., Zhang L., Ling J., Jian Y., Huang L, & Deng D. (2014). An In Vitro Study on the Effect of Free Amino Acids Alone or in Combination with Nisin on Biofilms as well as on Planktonic Bacteria of Streptococcus mutans. PLoS ONE, 9(6), e99513.

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Proline Stereoisomers Characterization

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The following compounds were purchased from Sigma: L-proline (product number P0380), D-proline (product number 858919), trans-4-hydroxy-L-proline (THLP, product number H54409), trans-4-hydroxy-D-proline (THDP, product number 702501), cis-4-hydroxy-D-proline (CHDP, product number H5877), cis-4-hydroxy-L-proline (CHLP, product number H1637).

Campbell A.C., Bogner A.N., Mao Y., Becker D.F, & Tanner J.J. (2020). Structural Analysis of Prolines and Hydroxyprolines Binding to the L-glutamate-γ-semialdehyde Dehydrogenase Active Site of Bifunctional Proline Utilization A. Archives of biochemistry and biophysics, 698, 108727.

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