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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:
1884944
EC Number:
219-468-4
MDL number:
MFCD00056670
UNSPSC Code:
12352100
PubChem Substance ID:
329750747
NACRES:
NA.22

Assay

≥98.0% (T)

functional group

amine

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

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

15149-VAR:
15149-BULK:
15149-10G:
15149-50G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0076
BCBW8912
BCBV5795
BCBV1031
BCBT6476

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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
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
C T Bailey et al.
Biochemistry, 36(33), 10105-10108 (1997-08-19)
The mechanism by which the iron-transport protein transferrin releases its iron in vivo is presently unclear. In vitro studies have implicated two concurrent chelator-mediated iron-release pathways: one which is hyperbolic in nature, involving a conformational change in the protein as
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
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
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