Gramine
| Gramine | |
|---|---|
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3-(dimethylamino |
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| Identifiers | |
| CAS number | 87-52-5  |
| ChemSpider | 6625 |
| KEGG | C08304 |
| ChEMBL | CHEMBL254348 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C11H14N2 |
| Molar mass | 174.24 g/mol |
| Melting point |
138-139 °C |
| Hazards | |
| NFPA 704 |
 1
2
0
|
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.[1]
Contents |
[edit] Occurrence
Gramine has been found in the Arundo donax[2][3],Acer saccharinum (Silver Maple)[4], Hordeum[1][3], and Phalaris[3] plant species.
[edit] Synthesis
Despite being widely available in several plant species, gramine is far easier to synthesize directly from indole via a Mannich reaction with dimethylamine and formaldehyde.
[edit] Uses
Gramine is used mostly in synthetic organic chemistry as a starting material for tryptophan syntheses.
All reactions of gramine follow the same general reaction scheme. Gramine is reacted with a strong electrophile, such as methyl iodide, to form the quaternary ammonium salt 2. The ammonium salt will undergo a Hofmann elimination or Michael addition to give the very active intermediate 3, which can accept a wide range of nucleophiles to give the desired product 4.
[edit] References
- ^ a b Corcuera, L. J. (1993). "Biochemical basis of the resistance of the barley to aphids". Phytochemistry 33 (4): 741–747. doi:10.1016/0031-9422(93)85267-U.
- ^ Orechoff,A. and Norkina,S. (1935). "Über die Alkaloide von Arundo Donax L". Berichte der deutschen chemischen Gesellschaft 68 (3): 436–437. doi:10.1002/cber.19350680312.
- ^ a b c Cheeke, Peter R. (1989). Toxicants of Plant Origin, Alkaloids. CRC Press. p. 172. ISBN 0-8493-6990-8. http://books.google.com/?id=eASgQyXq8xMC&pg=PA169&pg=172#v=onepage&q&f=false.
- ^ Pachter, Irwin J.; Zacharias, David E.; Ribeiro, Oscar (1959). "Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis". J. Org. Chem. 24 (9): 1285–1287. doi:10.1021/jo01091a032.
