10268. Aminoethoxyvinylglycine

Nomenclature

CAS number: 49669-74-1
(2S,3E)-2-Amino-4-(2-aminoethoxy)-3-butenoic acid; l-trans-2-amino-4-(2-aminoethoxy)butenoic acid.
C6H12N2O3; mol wt 160.17.
C 44.99%, H 7.55%, N 17.49%, O 29.97%.

Description and references

Inhibitor of 1-aminocyclopropane-1-carboxylate (ACC) synthase; applied to apples, pears, stone fruits, and walnuts to inhibit ethylene production and delay ripening. Amino acid antimetabolite produced by fermentation of Streptomyces. Prepn: J. Berger et al., US 3751459 (1973 to Hoffmann-La Roche); D. L. Pruess et al., J. Antibiot. 27, 229 (1974) PubMed. Synthesis of dl-form: D. D. Keith et al., J. Org. Chem. 43, 3713 (1978) DOI. Crystal structure in complex with ACC synthase: G. Capitani et al., J. Biol. Chem. 277, 49735 (2002) DOI PubMed. Mechanism of action study: M. E. Saltveit, Postharvest Biol. Technol. 35, 183 (2005) DOI.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 55720-26-8
ReTain (Valent).
C6H12N2O3.HCl; mol wt 196.63.
C 36.65%, H 6.66%, N 14.25%, O 24.41%, Cl 18.03%.

Properties

Crystals from methanol-H2O, mp 193-195°. [α]D25 +89.2° (c = 1 in 0.1M sodium phosphate buffer, pH 7). [α]D25 +111.8° (c = 1 in 5N HCl).

Derivative

dl-Form.

Nomenclature

CAS number: 69257-01-8; 67010-42-8 (hydrochloride)
(3E)-2-Amino-4-(2-aminoethoxy)-3-butenoic acid.

Properties

Hydrochloride as crystals from water/methanol, mp 187.5-189° (dec).

Use

Plant growth regulator.