Homoser
| Structural formula | ||||||||||||||||||||||
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| Structural formula of L homoserine | ||||||||||||||||||||||
| General | ||||||||||||||||||||||
| Surname | L homoser | |||||||||||||||||||||
| other names |
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| Molecular formula | C 4 H 9 NO 3 | |||||||||||||||||||||
| Brief description |
colorless solid |
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| properties | ||||||||||||||||||||||
| Molar mass | 119.12 g · mol -1 | |||||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
Decomposition: 203 ° C |
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| solubility |
easily soluble in water |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Homoserine is a non-proteinogenic, polar α- amino acid . It is derived from serine through an additional methylene group in the carbon chain.
Isomerism
Homoserine has a stereogenic center and thus has two enantiomers , L -homoserine [synonym: ( S ) -homoserine] and its mirror image, D -homoserine [synonym: ( R ) -homoserine]. The racemate DL -homoserin [synonym: ( RS ) -homoserin] consists in equal parts of L -homoserin and D -homoserin. When homoserine is mentioned in the scientific literature without any further addition, it almost always means L -homoserine.
| Isomers of homoserine | ||
| Surname | L homoser | D homoser |
| other names | ( S ) homoser | ( R ) homoser |
| Structural formula | |
-Homoserin_Structural_Formula_V.1.svg)
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| CAS number | 672-15-1 | 6027-21-0 |
| 1927-25-9 (unspec.) | ||
| EC number | 211-590-6 | 611-961-6 |
| 217-661-8 (unspec.) | ||
| ECHA info card | 100.010.538 | 100.111.579 |
| 100.016.057 (unspec.) | ||
| PubChem | 12647 | 2724170 |
| 779 (unspec.) | ||
| DrugBank | DB04193 | - |
| - (unspec.) | ||
| Wikidata | Q418214 | Q27113921 |
| Q27113920 (unspec.) | ||
biochemistry
L- homoserine is an intermediate product in the biochemical degradation of L - methionine .
L- homoserine is also formed in metabolism with L - cysteine from L - homocysteine with thiol transfer to L - serine with cystathionine synthase (1) and cystathionase (2) catalysis.
In this case, forms cystathionine as a temporary intermediate product from the condensation of L -serine with L homocysteine with elimination of water on the thiol or hydroxy-end. During the subsequent hydrolysis, L - cysteine and L- homoserine are produced again by splitting (2) .
- Failure (1) ⇒ homocysteinuria
- Failure (2) ⇒ cystathionuria
L -homoserine can split off ammonia under the influence of homoserine deaminase and is converted to α- ketobutyrate. This can be transaminated to the α - aminobutyrate or combine with CoA-SH to form propionyl-CoA with the recovery of NADH / H + and decarboxylation .
Manufacturing
L homoser is produced on an industrial scale by fermentation at the Evonik subsidiary Fermas in Slovenská Ľupča in Slovakia. The unnatural amino acid is thus made from renewable raw materials.
use
( S ) -Homoserine is a starting material for the production of numerous interesting organic-chemical intermediates, including the following heterocycles: ( S ) -3-aminopyrrolidine, ( S ) -3-aminobutyrolactone, ( S ) -3-aminotetrahydrothiophene, ( S. ) -3-aminotetrahydrofuran and ( S ) -azetidinecarboxylic acid.
Individual evidence
- ↑ a b data sheet homoserine (PDF) from Calbiochem, accessed on December 8, 2015.
- ↑ a b c data sheet L -homoserin at AlfaAesar, accessed on July 28, 2019 ( PDF )(JavaScript required) .
- ↑ a b Andreas Karau: Rosy prospects with white biotechnology , elements 30 , 2010, pp. 26–30.