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Z-(2R,3S)-AHPA, also known as Z-(2S,3R)-amino-2-hydroxy-3-methylpentanoic acid, is a structural isomer of L-threo-3-hydroxyaspartate. It is an amino acid derivative characterized by the presence of a hydroxyand a methylgroup attached to the alpha carbon. Z-(2R,3S)-AHPA has been identified as a potent antagonist of the glutamate receptor, specifically targeting the kainate subtype. Its ability to inhibit glutamate receptor-mediated neurotoxicity positions it as a potential therapeutic agent in the treatment of neurological disorders such as stroke and epilepsy. Furthermore, Z-(2R,3S)-AHPA has garnered interest for its capacity to modulate neurotransmission and synaptic plasticity within the brain.

59969-65-2

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  • (2S,3R)-3-{[(Benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid

    Cas No: 59969-65-2

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59969-65-2 Usage

Uses

Used in Pharmaceutical Industry:
Z-(2R,3S)-AHPA is used as a neuroprotective agent for its potential to inhibit glutamate receptor-mediated neurotoxicity, which is implicated in the pathophysiology of neurological disorders such as stroke and epilepsy. By blocking the excitotoxic effects of excessive glutamate, Z-(2R,3S)-AHPA may help reduce neuronal damage and improve patient outcomes.
Used in Neurological Research:
In the field of neuroscience, Z-(2R,3S)-AHPA is utilized as a research tool to study the role of glutamate receptors in synaptic transmission and plasticity. Its antagonistic properties allow researchers to investigate the mechanisms underlying neurological conditions and develop targeted therapies for various brain disorders.
Used in Drug Development:
Z-(2R,3S)-AHPA is employed in the development of novel therapeutics aimed at modulating neurotransmission and synaptic plasticity. Its ability to interact with specific glutamate receptor subtypes offers a unique opportunity to create drugs that can selectively target pathological processes in the brain, potentially leading to more effective treatments with fewer side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 59969-65-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,9,6 and 9 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 59969-65:
(7*5)+(6*9)+(5*9)+(4*6)+(3*9)+(2*6)+(1*5)=202
202 % 10 = 2
So 59969-65-2 is a valid CAS Registry Number.

59969-65-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S,3R)-3-{[(Benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:59969-65-2 SDS

59969-65-2Relevant articles and documents

Multifunctional immunity-targeted micromolecule anti-cancer medicine (Bestazomib citrate) and preparation method and application thereof

-

Paragraph 0017; 0067; 0068, (2019/01/11)

The invention discloses multifunctional immunity-targeted micromolecule anti-cancer medicine (Bestazomib citrate) and a preparation method and application thereof. A structure of the multifunctional immunity-targeted micromolecule anti-cancer medicine (Be

Novel synthesis of (-)-bestatin from L-aspartic acid

Seki, Masahiko,Nakao, Kazuya

, p. 1304 - 1307 (2007/10/03)

Oxazoline-4-acetate derivative 3 that could be readily obtained from L-aspartic acid was subjected to highly stereoselective hydroxylation, and subsequent Mitsunobu inversion of the hydroxyl group led to (2S,3R)-3-amino-3-benzyl-2-hydroxybutanoic acid der

Ring opening of optically active cis-disubstituted aziridino alcohols: An enantiodivergent synthesis of functionalized amino alcohol derivatives

Fuji, Kaoru,Kawabata, Takeo,Kiryu, Yoshimitsu,Sugiura, Yukio

, p. 701 - 722 (2007/10/03)

Ring-opening reactions of optically active cis-disubstituted aziridino alcohols have been investigated. Regio- and stereo-selective ring opening took place with internal and external nucleophiles. Unusual amino acids derivatives (14) and (15), the key synthetic intermediates for bestatin and related peptides, have been prepared. n.

An enantiodivergent synthesis of three β-amino alcohols: Preparation of key intermediates for bestatin and the related peptides

Kawabata,Kiryu,Sugiura,Fuji

, p. 5127 - 5130 (2007/10/02)

An enantiodivergent method for preparation of three β-amino alcohols and three 1,2-diamines has been developed starting with a chiral aziridine 1. Unusual amino acid derivatives 3 and 5, which are key synthetic intermediates for bestatin and the related peptides, have been prepared.

Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates

Herranz, Rosario,Castro-Pichel, Julia,Garcia-Lopez, Teresa

, p. 703 - 706 (2007/10/02)

Reaction of tributyltin cyanide with optically active 2-N-benzyloxycarbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively.Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzyloxycarbonylam

A STEREOCONTROLLED SYNTHESIS OF (-)-BESTATIN FROM AN ACYCLIC ALLYLAMINE BY IODOCYCLOCARBAMATION

Kobayashi, Susumu,Isobe, Toshiyuki,Ohno, Masaji

, p. 5079 - 5082 (2007/10/02)

1,2-Asymmetric induction of iodocyclocarbamation is described by using allylamines 2 and 6 and the method has been succesfully applied to a stereocontrolled synthesis of bestatin.

Process for producing threo-3-amino-2-hydroxybutanoyl-aminoacetic acids, as well as novel intermediated therefor and process for producing them

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, (2008/06/13)

A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: STR1 wherein R1 represents a naphthyl or a group of the formula: STR2 in which R6 and R7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R2 represents a protected amino, with a starting compound represented by the general formula: STR3 wherein R3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: STR4 wherein R1, R2 and R3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: STR5 wherein R1, R2 and R3 have the same meanings as above, and further converting the above compound into 3-amino-2-hydroxybutanoic acid represented by the general formula: STR6 wherein R2 ' represents amino or a protected amino, thereafter condensing the same, in a conventional manner for forming a peptide coupling, with a compound represented by the general formula: STR7 wherein R4 represents an alkyl having 3-4 carbon atom or 3-guanidinopropyl, while previously protecting as required those groups not relevant to the reaction, and removing the protecting groups for the functional groups to produce threo-3-amino-2-hydroxybutanoylaminoacetic acids represented by the general formula: STR8 wherein R1 and R4 have the same meanings as above. This invention also provides the compounds represented by the general formula (III) as novel intermediates for the above aimed compounds and a process for producing the intermediates.

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