23220-52-2

Basic information

• Product Name: MESO-2 3-DIAMINOSUCCINIC ACID
• Synonyms: erythro-3-aminoaspartic acid;(2R,3S)-diaminosuccinic acid;(2R,3S)-2,3-Diaminosuccinic acid;(3R)-3-Amino-L-aspartic acid;Einecs 245-500-1
• CAS NO: 23220-52-2
• Molecular Formula: C₄H₈N₂O₄
• Molecular Weight: 148.11732
• EINECS: 245-500-1
• Product Categories: Others;Peptide Synthesis;Unnatural Amino Acid Derivatives;amino
• Mol File: 23220-52-2.mol

Chemical Properties

• Melting Point: 304 °C
• Boiling Point: 304.7 °C at 760 mmHg
• Flash Point: 138.1 °C
• Appearance: /
• Density: 1.611 g/cm³
• Vapor Pressure: 0.000197mmHg at 25°C
• Refractive Index: 1.582
• PKA: 1.43±0.27(Predicted)
• CAS DataBase Reference: MESO-2 3-DIAMINOSUCCINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: MESO-2 3-DIAMINOSUCCINIC ACID(23220-52-2)
• EPA Substance Registry System: MESO-2 3-DIAMINOSUCCINIC ACID(23220-52-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 23220-52-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
MESO-2,3-Diaminosuccinic Acid is used as a building block in organic synthesis for the development of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
MESO-2,3-Diaminosuccinic Acid is used in the synthesis of metal complexes for their antitumor activity. These metal complexes have shown potential in targeting and treating various types of cancer, making them a valuable tool in the fight against this deadly disease.

Purification Methods

Crystallise the acid from water. Also, dissolve it in dilute NaOH and add AcOH to pH 5-6 and allow it to crystallise (m 304o dec). Alternatively dissolve the acid in aqueous NH3 and boil; when the NH3 has evaporated, the acid separates, filter it off and dry it at room temperature in a vacuum. In another procedure 1g of acid is dissolved in 10mL of conc HCl + 15mL of H2O at 80o, filter immediately, dilute with 20mL of H2O and allow to stand for 24hours. When the monohydrochloride (0.7g, m 175-156o dec) crystallises out, filter and dry it. It has also been purified by dissolving it in the minimum volume of 10% HCl, filtering, and diluting with 5volumes of H2O when the crystals separate slowly on standing. The acid is filtered off after 24hours and dried (m 306-306o dec). Similar procedures were used for the dl-isomer. [Kenner J Org Chem 13 28 1948, McKennis & Yard J Org Chem 23 980 1958, Beilstein 4 III 1528, 4 IV 3025.]

InChI:InChI=1/C4H8N2O4/c5-1(3(7)8)2(6)4(9)10/h1-2H,5-6H2,(H,7,8)(H,9,10)

Upstream product

• 93143-54-5 2,3-Diformamino-2,3-diaethoxycarbonyl-bernsteinsaeure-diaethylester 
• 89-06-5 bis-phenylhydrazono-succinic acid 
• 7647-01-0 hydrogenchloride 
• 53079-45-1 racem-2,3-bis-benzylamino-succinic acid 
• 64-19-7 acetic acid 
• 479622-98-5 1-carbamoyl-aziridine-2,3-dicarboxylic acid diethyl ester 
• 101349-74-0 2,2-Dibromo-succinic acid 
• 55645-40-4 (2R,3S)-2,3-bis(benzylamino)succinic acid 

Downstream Products

• 147-73-9 meso-tartaric acid 
• 3856-37-9 (2R,3S)-2,3-Dichloro-succinic acid 
• 608-36-6 meso-2,3-dibromosuccinic acid 
• 87-69-4 tartaric acid 
• 133-37-9 DL-tartaric acid 
• 526-78-3 2,3-dibromosuccinic acid 

Relevant articles and documents

CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP

Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.

Asymmetric Oxidative Dimerization of the Enolates of N-[Bis(methylthio)methylene]- and N-(Diphenylmethylene)glycine Esters

The oxidative dimerization of glycinates 1 with iodine takes place under kinetic control. The stereochemistry of the resulting 3-aminoaspartate 3 depends on the method used (base/solvent) to generate the corresponding enolate 2. Under suitable conditions, high yields and diastereomeric excesses in favor of the threo derivatives 3-I, which have C2 symmetry, were obtained. In the presence of 8-phenylmenthol as chiral auxiliary (25, 3S)-3-aminoaspartic acid 5-I was synthesized.

Oxidation of Alkenes and Sulfides with Transition Metal Catalysts

Alkenes and sulfides were oxidized with transition-metal catalysts.The oxidant sources include molecular dioxygen, air and iodosylbenzene.The metal ions Mn(III), Fe(III), Co(II) and Ni(II) were used.The catalysts 1-18 of 1,3-dioxo-, β-ketoimine- or salen-types were prepared and their efficacy was examined. 1,2-Dihydronaphthalene is most efficiently epoxidized with O2/Me2CHCHO or PhIO in the presence of Mn(III)-salen catalysts.The Ni(II)-, Co(II)- and Fe(III)-catalysts of either β-ketoimine- or salen-types are useful for epoxidation of styrene, (E)-stilbene and (E)-benzalacetone in the O2/Me2CHCHO system; these epoxidations are stereospecific without formation of corresponding diastereomeric epoxides.Oxidation of methyl p-totyl sulfide with O2/Me2CHCHO is facilitated by the 1,3-dioxo-catalyst Co(II)-1.Monooxidation is achieved with Me2CHCHO in equimolar proportions to give the corresponding sulfoxide, whereas overoxidation is realized with excess Me2CHCHO to give the sulfone.These epoxidation and sulfide oxidations all occur at 25 deg C and are complete in less than a day.Key Words: Oxidation; Transition metals; Alkenes; Sulfides; 1,3-Diketone; β-Ketoimine; Salen.