Isolation of Biliverdin Ixa, as Its Dimethyl Ester, from Emu Eggshells

Autor/inn/en	Halepas, Steven; Hamchand, Randy; Lindeyer, Samuel E. D.; Bru¨ckner, Christian
Titel	Isolation of Biliverdin Ixa, as Its Dimethyl Ester, from Emu Eggshells
Quelle	In: Journal of Chemical Education, 94 (2017) 10, S.1533-1537 (5 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Zusatzinformation	ORCID (Hamchand, Randy) ORCID (Bru¨ckner, Christian)
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
DOI	10.1021/acs.jchemed.7b00449
Schlagwörter	Animals; Science Instruction; Laboratory Experiments; Chemistry; Spectroscopy; Organic Chemistry; Undergraduate Students; College Science; Laboratory Procedures; Science Experiments; Biology; Color; Science Activities; Molecular Structure; Connecticut + Suchen Sie Ihr Suchwort? Animal; Tier; Tiere; Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht; Laboratory work; Laborarbeit; Chemie; Spektroskopie; Organische Chemie; Laboruntersuchung; Biologie; Colour; Farbbezeichnung; Farbe
Abstract	A laboratory experiment is described that extracts the tetrapyrrolic teal-colored biliverdin IXa, as its dimethyl ester, from commercially available emu eggshells. The extraction of ~10 mg samples of biliverdin is simple and requires two 3 h lab periods: A two-step acid digestion and liquid-liquid extraction, followed by short silica gel flash column chromatography. The deeply colored extract can be characterized by TLC, UV-vis, IR, [superscript 1]H NMR spectroscopy, ESI+ mass spectrometry, or its diagnostic chemical reduction to the yellow derivative bilirubin. A small-scale variant of this extraction requires only a single 3 h lab period, and the extracts can be analyzed by UV-vis spectroscopy, ESI[superscript +] MS, or HPLC. An introduction to the biological origin of biliverdin is provided. This pedagogically flexible project combines natural product isolation with the spectroscopic characterization of a multifunctional biomedically important compound and touches upon many aspects of chemistry and biology. The colorful experiment is appropriate for the introductory organic chemistry laboratory and possesses the prerequisites for a chemistry-biology interlaboratory approach. (As Provided).
Anmerkungen	Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2020/1/01