Cyclovaline
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| General | |||||||||||||||||||
| Surname | Cyclovaline | ||||||||||||||||||
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| Molecular formula | C 5 H 9 NO 2 | ||||||||||||||||||
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| Molar mass | 115.13 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
270-272 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Cyclovaline is a non-proteinogenic α- amino acid and can be regarded as a cyclic derivative of norvaline . It differs from this u. a. due to a molecular weight lower by two hydrogen atoms . The defining structural element is a cyclobutane ring. The α- carbon atom is also not a stereocenter , so cyclovaline is not chiral .
properties
Similar to other amino acids, cyclovaline is predominantly a zwitterion , the formation of which can be formally explained by the fact that the proton of the carboxy group migrates to the lone pair of electrons on the nitrogen atom of the amino group.
The zwitterion does not migrate in the electric field because it is uncharged as a whole. Strictly speaking, this is the case at the isoelectric point (at a certain pH value), at which the cyclovaline also has its lowest solubility in water.
synthesis
Starting from diethyl malonate and 1,3-dibromopropane , the heterocycle cyclobutane- spiro -5'- hydantoin is produced. Its hydrolysis with sodium hydroxide solution and subsequent neutralization with hydrochloric acid then yields cyclovaline.
Individual evidence
- ↑ a b R. JW Cremlyn: “Some New Alicyclic α-Amino-acids”, in: Journal of the Chemical Society , 1962 , pp. 3977-3980; doi: 10.1039 / JR9620003977 .
- ↑ a b Data sheet 1-Amino-1-cyclobutanecarboxylic acid from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).