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A5352

L-(+)-2-Amino-6-phosphonohexanoic acid

Name: <SC>L</SC>-(+)-2-Amino-6-phosphonohexanoic acid
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

L-AP6

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₄NO₅P

CAS Number:

126253-57-4

Molecular Weight:

211.15

MDL number:

MFCD00144531

UNSPSC Code:

12352200

PubChem Substance ID:

24724392

NACRES:

NA.77

assay

≥98% (HPLC)

form

solid

color

white

SMILES string

N[C@@H](CCCCP(O)(O)=O)C(O)=O

InChI

1S/C6H14NO5P/c7-5(6(8)9)3-1-2-4-13(10,11)12/h5H,1-4,7H2,(H,8,9)(H2,10,11,12)/t5-/m0/s1

InChI key

QIOXWRQXHFVNLV-YFKPBYRVSA-N

Biochem/physiol Actions

L-(+)-2-Amino-6-phosphonohexanoic acid (L-AP6) is an excitatory glutamate analogue that is able to depolarize L-quisqualic acid (QUIS)-sensitized CA1 rat hippocampal neurons.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L-Quisqualic acid transport into hippocampal neurons by a cystine-sensitive carrier is required for the induction of quisqualate sensitization.

L A Chase et al.

Neuroscience, 106(2), 287-301 (2001-09-22)

A brief exposure of hippocampal slices to L-quisqualic acid sensitizes CA1 pyramidal neurons 30-250-fold to depolarization by two classes of excitatory amino acid analogues: (1) those whose depolarizing effects are rapidly terminated following washout, e.g. L-2-amino-4-phosphonobutanoic acid (L-AP4) and L-2-amino-6-phosphonohexanoic

The lathyrus toxin, beta-N-oxalyl-L-alpha,beta-diaminopropionic acid (ODAP), and homocysteic acid sensitize CA1 pyramidal neurons to cystine and L-2-amino-6-phosphonohexanoic acid.

L A Chase et al.

Toxicology and applied pharmacology, 219(1), 1-9 (2007-01-20)

A brief exposure of hippocampal slices to L-quisqualic acid (QUIS) sensitizes CA1 pyramidal neurons 30- to 250-fold to depolarization by certain excitatory amino acids analogues, e.g., L-2-amino-6-phosphonohexanoic acid (L-AP6), and by the endogenous compound, L-cystine. This phenomenon has been termed

Utilization of the resolved L-isomer of 2-amino-6-phosphonohexanoic acid (L-AP6) as a selective agonist for a quisqualate-sensitized site in hippocampal CA1 pyramidal neurons.

M K Schulte et al.

Brain research, 649(1-2), 203-207 (1994-06-27)

Brief exposure of rat hippocampal slices to quisqualic acid (QUIS) sensitizes neurons to depolarization by the alpha-amino-omega-phosphonate excitatory amino acid (EAA) analogues AP4, AP5 and AP6. These phosphonates interact with a novel QUIS-sensitized site. Whereas L-AP4 and D-AP5 cross-react with

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