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15149

Sigma-Aldrich

N,N-Bis(phosphonomethyl)glycine

≥98.0% (T)

Synonym(s):

N-(Carboxymethyl)iminodi(methylphosphinic acid), Glyphosine

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About This Item

Empirical Formula (Hill Notation):
C4H11NO8P2
CAS Number:
2439-99-8
Molecular Weight:
263.08
Beilstein/REAXYS Number:
1884944
EC Number:
219-468-4
MDL number:
MFCD00056670
UNSPSC Code:
12352100
PubChem Substance ID:
329750747
NACRES:
NA.22

Quality Level

100

assay

≥98.0% (T)

SMILES string

O=P(CN(CP(O)(O)=O)CC(O)=O)(O)O

InChI

1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13)

InChI key

OXHDYFKENBXUEM-UHFFFAOYSA-N

General description

N,N-Bis(phosphonomethyl)glycine was present in the ligand bound to human apotransferrin.

Application

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.†

Biochem/physiol Actions

Anti-diabetic; delay onset of diabetes in non-obese NOD mice

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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L J Olson et al.
Toxicology, 30(2), 103-114 (1984-03-01)
Exposure to the plant growth regulators, chlorocholine chloride (CCC) and glyphosine (GPS), resulted in significant immunomodulatory effects after feeding to deer mice (Peromyscus maniculatus) for 28 days. Cyclophosphamide (CP) and saline controls were included. Both CCC and GPS feeding levels
Markus Galanski et al.
Journal of medicinal chemistry, 46(23), 4946-4951 (2003-10-31)
A series of osteotropic (bone-seeking) [(bis(phosphonomethyl)amino-kappaN)acetato-kappaO(2-)]platinum(II) complexes attached to diammine, ethane-1,2-diamine, cis-R,S-cyclohexane-1,2-diamine, trans-S,S-cyclohexane-1,2-diamine, or trans-R,R-cyclohexane-1,2-diamine has been synthesized in accord with the concept of drug targeting and characterized by elemental analysis, (1)H, (13)C, and (31)P NMR spectroscopy. The in vitro
W R Harris et al.
Biochemistry, 30(28), 6930-6936 (1991-07-16)
Difference ultraviolet spectroscopy has been used to monitor the binding of a series of phosphonate ligands to human apotransferrin. The ligands consist of pyrophosphate as well as the phosphonic acids (aminomethyl)phosphonic acid (AMPA), (hydroxymethyl)phosphonic acid (HMP), (phosphonomethyl)-iminodiacetic acid (PIDA), N,N-bis(phosphonomethyl)glycine
Aaron W Michels et al.
Journal of immunology (Baltimore, Md. : 1950), 187(11), 5921-5930 (2011-11-02)
Class II major histocompatibility molecules are the primary susceptibility locus for many autoimmune disorders, including type 1 diabetes. Human DQ8 and I-A(g7), in the NOD mouse model of spontaneous autoimmune diabetes, confers diabetes risk by modulating presentation of specific islet
Aurelia Visa et al.
Nanomaterials (Basel, Switzerland), 10(5) (2020-05-14)
The rapid increase of industrial activities leads to serious environmental pollution, especially, in aqueous systems and particularly with heavy metals. Cadmium, one of the most poisonous elements, is rapidly accumulated in the human body, therefore, the efficient removal of cadmium
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