5499. Linatine

Nomenclature

CAS number: 10139-06-7
1-[(4-Amino-4-carboxy-1-oxobutyl)amino]-d-proline; N-(d-2-carboxy-1-pyrrolidinyl)-l-glutamine; 1-[N-(γ-l-glutamyl)amino]-d-proline.
C10H17N3O5; mol wt 259.26.
C 46.33%, H 6.61%, N 16.21%, O 30.86%.

Description and references

A vitamin B6 antagonist. The first reported naturally occurring hydrazino acid having antibacterial properties. Isoln from flaxseed (Linum usitatissimum), characterization, and synthesis: Klosterman et al., Biochemistry 6, 170 (1967); Lamoureux, Diss. Abstr. B 28, 4908 (1968). Bacterial inhibition: Parsons et al., Antimicrob. Agents Chemother. 1967, 415.

Chemical structure

Properties

Amorphous powder. [α]D25 +46.4° (c = 2.8 in water). Attempts to obtain well-defined crystals have failed; melts with dec over a wide temperature range. Very sol in water. Practically insol in anhydr organic solvents.

Derivative

l-Isomer.

Properties

Amorphous solid. [α]D24 34.6° (c = 2 in water).