Glyphosine was introduced in 1973 and is preferably used in sugar beets. The synthesis starting with glycine uses two equivalents of formaldehyde and of phosphorous trichloride under oxidative conditions. A second derivative of Glyphosate is a cyclic phosphaoxazole being formed from Glyphosate and formaldehyde. This compound is claimed to control the growth of some grasses without dis- coloration or phytotoxicity.
Chemical ripener; plant growth regulator.
Application: Complexing agent; pK-values: pK1: ·2, pK2: 2.0, pK3: 5.20, pK4: 6.77, pK5: 10.89
Anti-diabetic; delay onset of diabetes in non-obese NOD mice
Glyphosine binds to a pocket of MHC class II molecules I-Ag7 and DQ8, and modify T cell responses to the autoantigenic insulin B chain fragment 9–23 (B:9–23) peptide. Glyphosine stimulate IL-10 production and delay onset of diabetes in non-obese NOD mice.
ChEBI: A tertiary amino compound that consists of glycine bearing two N-phosphonomethyl substituents.
Detailed information on the synthesis of glyphosine is not readily available in open literature. However, it was probably produced through a multistep process typical of aminomethyl phosphonate herbicides, beginning with the preparation of an amino acid–derived intermediate such as iminodiacetic acid or a substituted glycine analogue. Industrial manufacturers introduce the phosphonomethyl group via reaction with phosphorus trichloride and formaldehyde under controlled acidic conditions, forming a phosphonomethylated amino acid similar to the PMIDA and glycine based routes documented for glyphosate production. This condensation–oxidation sequence is followed by hydrolysis and neutralisation to yield the free acid or salt form of glyphosine. Purification typically involves aqueous work up, pH adjustment, and crystallisation to achieve technical grade purity
N,N-Bis(phosphonomethyl)glycine was present in the ligand bound to human apotransferrin.
Anti-diabetic; delay onset of diabetes in non-obese NOD mice
Absorbed by foliage and translocated, increases the partioning of dry matter towards sucrose storage and away from fibre production
Plant Growth Regulator; Herbicide
