Azetidine-2-carboxylic acid

• (S)- azetidinecarboxylic acid
• (S)- azetidine-2 -carboxylic acid
• L- azetidine carboxylic acid
• L- azetidine-2 -carboxylic acid
• (R)- azetidine carboxylic acid
• (R)- azetidine-2 -carboxylic acid
• D- azetidinecarboxylic
• D- azetidine-2 -carboxylic acid

• 2133-34-8 [(S) -azetidine -2-carboxylic acid]
• 7729-30-8 [(R) -azetidine -2-carboxylic acid]
• 20063-89-2 [( R / S) -azetidine -2-carboxylic acid]

Beige solid

Fixed

217 ° C.

5 % in water

1000 mg · kg -1 ( LD50, mouse, s.c )

Template: Infobox chemical / molecular formula search available

(S)- azetidine-2 -carboxylic acid is a non- canonical α - amino acid from the group of Azetidincarbonsäuren that differs from its analog, of the proteinogenic amino acid L- proline [(S) -proline ] only by ring contraction to a methyl group. It is a toxic component of the rhizomes of native lily of the valley and has an inhibitory effect on plant growth. The azetidine-2 -carboxylic acid, has a stereogenic center, so it is chiral. There are two enantiomers: (S)- azetidine-2 -carboxylic acid and (R)- azetidine-2 -carboxylic acid. The latter has little meaning.

Natural Occurrence

In addition to the parent drug ( S)- azetidine- 2-carboxylic acid [ synonym: L -azetidine -2-carboxylic acid] come in lily of the valley (Convallaria majalis ) and sugar beet in nature especially their derivatives: Mugineinsäure serves as phytosiderophores and nicotianamine in soy sauce included.

Toxic effect on predators

If predators ( herbivores ) eat the lily of the valley and thus the poison, (S) -azetidine -2 -carboxylic acid instead of ( S)- proline [ Synonym: L- proline ] installed in protein biosynthesis of feeding the enemy. As a result, changes the tertiary structure of newly synthesized proteins, so that they act unfit or even toxic in their biological activity.

The lily of the valley itself may be due to a highly specific prolyl -tRNA synthetase uncontrolled incorporation of ( S)- azetidine- 2-carboxylic acid [ synonym: L -azetidine -2-carboxylic acid] deal in species-specific proteins.

Synthesis and Application

There are described a number of syntheses of (S)- azetidine-2 -carboxylic acid as well as the racemate in the literature. Generally azetidines can be obtained by reduction of β - lactams. Derivatives of azetidine be (, melagatran ABT -594 as a non-opioid analgesic as a thrombin inhibitor) used as medications, as pesticides as well as catalysts. The synthesis and use of (S) -azetidine -2-carboxylic acid derivatives as catalysts in the enantioselective borane reduction of prochiral ketones will be described in the literature.