Abstract
Water-soluble aldehydes (acetaldehyde, propionaldehyde) and non-water-soluble aldehydes (butyraldehyde and phenylacetaldehyde) were easily detected by an efficient fluorescent method with 5-aminofluorescein as probe. Under optimal detection conditions, 5-aminofluorescein could selectively respond to aldehydes with high sensitivity in comparison with other carbonyl compounds like ketones and acids. Thus, the proposed method was used to monitor microbial oxidation and succeeded in trapping transiently-produced aldehydes during biotransformation of primary alcohols by Gluconobacter oxydans.
Similar content being viewed by others
References
Committee on Toxicology and Environmental Health Hazards (1981) Formaldehydes and other aldehydes. National Academy Press, Washington, DC
Patterson RLS, Charlwood BV, MacLeod G, Williams AA (1992) In: Schreier P (ed) Bioflavours: an overview. The Royal Society of Chemistry Press, Cambridge, pp 1–20
Kotzias D, Konidari C, Sparta C (1997) In: Helas G, Slanina J, Steinbrecher R (eds) Biogenic volatile organic carbon compounds in the atmosphere. SPB Academic Publishing, Amsterdam, pp 67–78
Atkinson R (1990) Gas-phase tropospheric chemistry of organic compounds: a review. Atmos Environ 24A:1–41
Keiko NA, Stepanova LG, Kleptsova EA, Vdovina GP, Odegova TF (2009) Synthesis and antimicrobial activity of new aldehydes and acetals. Pharm Chem J 43:502–504
Noma Y, Akehi E, Miki N, Asakawa Y (1992) Biotransformation of terpene aldehydes, aromatic aldehydes and related compounds by Dunaliella tertiolecta. Phytochemistry 31:515–517
Gandolfi R, Ferrara N, Molinari F (2001) An easy and efficient method for the production of carboxylic acids and aldehydes by microbial oxidation of primary alcohols. Tetrahedron Lett 42:513–514
Asai T (1968) Acetic acid bacteria: classification and biochemical activities. University of Tokyo Press, Tokyo
Svitel J, Sturdik E (1995) n-Propanol conversion to propionic acid by Gluconobacter oxydans. Enzyme Microb Technol 17:546–550
Molinari F, Villa R, Aragozzini F, Cabella P, Barbeni M (1997) Multi-gram scale production of aliphatic carboxylic acids by oxidation with Acetobacter pasteurianus. J Chem Technol Biotechnol 70:294–298
Molinari F, Gandolfi R, Aragozzini F, Lèon R, Prazeres DMF (1999) Lyophilised yeasts: easy-to-handle biocatalysts for stereoselective reduction of carbonyls. Enzyme Microb Technol 25:729–735
Vogel M, Büldt A, Karst U (2000) Hydrazine reagents as derivatizing agents in environmental analysis—a critical review. Fresenius J Anal Chem 366:781–791
Hantzsch A (1882) Ueber die Synthese pyridinartiger Verbindungen aus Acetessigäther und Aldehydammoniak. Justus Liebigs Ann Chem 215:1–82
Bartos J, Pesez M (1979) Colorimetric and fluorimetric determination of aldehydes and ketones. Pure Appl Chem 51:1803–1814
Büldt A, Karst U (1997) 1-Methyl-1-(2, 4-dinitrophenyl) hydrazine as a new reagent for the HPLC determination of aldehydes. Anal Chem 69:3617–3622
Levin JO, Andersson K, Lindahl R, Nilson CA (1985) Determination of sub-part-per-million levels of formaldehyde in air using active or passive sampling on 2, 4-dinitrophenylhydrazine-coated glass fiber filters and high-performance liquid chromatography. Anal Chem 57:1032–1035
Van Hoof F, Wittocx A, Van Buggenhout E, Janssens J (1985) Determination of aliphatic aldehydes in waters by high-performance liquid chromatography. Anal Chim Acta 169:419–420
Chiavari G, Bergamini C (1985) High-performance liquid chromatography of carbonyl compounds as 2, 4-dinitrophenylhydrazones with electrochemical detection. J Chromatogr 318:427–432
Toyooka T, Liu Y-M (1995) Determination of aldehydes by high-performance liquid chromatography with fluorescence detection after labelling with 4-(2-carbazoylpyrrolidin-1-yl)-7-(N, N-dimethylaminosulfonyl) 2, 1, 3-benzoxa- diazole. J Chromatogr A 695:11–18
Stashenko EE, Ferreira MC, Sequeda LG, Martinez JR, Wong JW (1997) Comparison of extraction methods and detection systems in the gas chromatographic analysis of volatile carbonyl compounds. J Chromatogr A 779:360–369
Nondek L, Milofsky RE, Birks JW (1991) Determination of carbonyl compounds in air by HPLC using on-line analyzed microcartridges, fluorescence and chemiluminescence detection. Chromatographia 32:33–39
Uzu S, Kanda S, Imai K, Nakashima K, Akiyama S (1990) Fluorogenic reagents: 4-aminosulphonyl-7-hydrazino-2, 1, 3-benzoxadiazole, 4-(N, N-dimethy- -laminosulphonyl)-7-hydrazino-2, 1, 3-benzoxadiazole and 4-hydrazino-7-nitro- -2, 1, 3-benzoxadiazole hydrazine for aldehydes and ketones. Analyst 115:1477–1482
Konarzycka-Bessler M, Bornscheuer UT (2003) A high-throughput—screening method for determining the synthetic activity of hydrolases. Angew Chem Int Ed 42:1418–1420
Yang R, Li K, Li N, Zhao FL, Chan WH (2003) 3, 3′, 5, 5′-tetramethyl-N-(9-anthrylmethyl)benzidine: a dual-signaling fluores—cent reagent for optical sensing of aliphatic aldehydes. Anal Chem 75:3908–3914
Bajorek A, Trzebiatowska K, Jedrzejewska B, Pietrzak M, Gawinecki R, Paczkowski J (2004) Developing of fluorescence probes based on stilbazolium salts for monitoring free radical polymerization processes. II. J Fluoresc 14:295–307
Xi P, Xu Z, Liu X, Chen F, Zeng Z, Zhang X, Liu Y (2009) Synthesis, characterization, antioxidant activity and DNA-binding studies of three rare earth (III) complexes with 1-(4-aminoantipyrine)-3-tosylurea ligand. J Fluoresc 19:63–72
Molinari F, Villa R, Manzoni M, Aragozzini F (1995) Aldehyde production by alcohol oxidation with Gluconobacter oxydans. Appl Microbiol Biotechnol 43:989–994
Munkholm C, Parkinson DR, Walt DR (1990) Intramolecular fluorescence self-quenching of fluoresceinamine. J Am Chem Soc 112:2608–2612
De S, Das S, Girigoswami A (2005) Environmental effects on the aggregation of some xanthene dyes used in lasers. Spectrochim Acta A 61:1821–1833
Valdes-Aguilera O, Necbees DC (1989) Aggregation phenomena in xanthene dyes. Acc Chem Res 22:171–177
Baker DC, Frietag-Beeston RA, Whitten DG (1991) Atroplsomer-SpecHlc formatlon of premicellar porphyrin J-aggregates in aqueous surfactant solutions. J Phys Chem 95:4074–4086
Birks JB, Dyson DJ (1963) The relations between the fluorescence and absorption properties of organic molecules. Proc R Soc Lond, A Math Phys Sci 275:135–148
Tang B, Zhang L, Hu J, Li P, Zhang H, Zhao Y (2004) Indirect determination of superoxide anion radical in the plant of red sage based on vanillin-8-aminoquinoline with fluorescence. Anal Chim Acta 502:125–131
Houdier S, Perrier S, Defrancq E, Legrand M (2000) A new fluorescent probe for sensitive detection of carbonyl compounds: sensitivity improvement and application to environmental water samples. Anal Chim Acta 412:221–223
Acknowledgements
This work was supported by the National Basic Research Program of China (973 program, No. 2009CB724703).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xing, Y., Wang, S., Mao, X. et al. An Easy and Efficient Fluorescent Method for Detecting Aldehydes and Its Application in Biotransformation. J Fluoresc 21, 587–594 (2011). https://doi.org/10.1007/s10895-010-0746-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-010-0746-6