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3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID, also known as Aminoethyl-SS-propionic acid, is a cleavable compound that features a terminal amine and carboxylic acid group. It is characterized by its disulfide bonds, which can be cleaved using Dithiothreitol (DTT) reagent. 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID is a white solid and is known for its ability to react with various chemical groups, making it a versatile molecule in the field of biochemistry.

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  • 15579-00-7 Structure
  • Basic information

    1. Product Name: 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID
    2. Synonyms: Aminoethyl-SS-propionic acid
    3. CAS NO:15579-00-7
    4. Molecular Formula: C5H11NO2S2
    5. Molecular Weight: 181.28
    6. EINECS: N/A
    7. Product Categories: Nitric Oxide Reagents;Cross Linking Reagents;Amines;Sulfur & Selenium Compounds
    8. Mol File: 15579-00-7.mol
  • Chemical Properties

    1. Melting Point: 138-141oC
    2. Boiling Point: 339.5 °C at 760 mmHg
    3. Flash Point: 159.1 °C
    4. Appearance: white solid
    5. Density: 1.32 g/cm3
    6. Vapor Pressure: 1.69E-05mmHg at 25°C
    7. Refractive Index: 1.589
    8. Storage Temp.: -20°C Freezer
    9. Solubility: Soluble in Water, DMSO
    10. PKA: 4.20±0.10(Predicted)
    11. CAS DataBase Reference: 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID(15579-00-7)
    13. EPA Substance Registry System: 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID(15579-00-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 15579-00-7(Hazardous Substances Data)

15579-00-7 Usage

Uses

Used in Biochemistry and Molecular Biology:
3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID is used as a reversible immobilization or crosslinking reagent for various applications in biochemistry and molecular biology. The terminal amine can react with carboxylic acid, activated NHS esters, and other carbonyl compounds, while the terminal carboxylic acid can form a stable amide bond with primary amines in the presence of activators such as EDC and HATU. This reagent is particularly useful for the study of protein-protein interactions, enzyme immobilization, and the development of biosensors.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID is used as a key component in the development of drug delivery systems. Its ability to form stable amide bonds and react with various chemical groups makes it an ideal candidate for the design of targeted drug delivery systems, which can improve the efficacy and bioavailability of therapeutic agents.
Used in Materials Science:
3-[(2-AMINOETHYL)DITHIO]PROPIONIC ACID is also utilized in materials science for the development of novel biocompatible materials. Its chemical properties allow for the creation of materials with specific interactions and functionalities, which can be applied in areas such as tissue engineering, biosensors, and drug delivery devices.

Check Digit Verification of cas no

The CAS Registry Mumber 15579-00-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,5,7 and 9 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 15579-00:
(7*1)+(6*5)+(5*5)+(4*7)+(3*9)+(2*0)+(1*0)=117
117 % 10 = 7
So 15579-00-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2S2/c6-2-4-10-9-3-1-5(7)8/h1-4,6H2,(H,7,8)

15579-00-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(2-aminoethyldisulfanyl)propanoic 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

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15579-00-7 SDS

15579-00-7Relevant articles and documents

DOLASTATIN 10 ANALOG

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Page/Page column 47; 49, (2021/05/07)

Provided herein is a dolastatin 10 analog, useful for preparing conjugates thereof with targeting, diagnostic, imaging and other moieties. Also provided are the conjugates and uses thereof.

Based on the response of the GSH treatment integrated organic molecular probe and its preparation method (by machine translation)

-

Paragraph 0085; 0086; 0087; 0088, (2017/06/13)

The invention discloses a treatment based on GSH response of the integrated organic molecular probe and its preparation method, constructing a type based on near-infrared fluorescent dye and tumor micro environment for diagnosis and treatment of integrated molecular Image probe, GSH can be cut off by oxidation-reduction function of the disulfide bond in the probe, the release of the active drug, the drug can be monitored with the purpose of the transmission of the release. The invention synthetic process is relatively simple and rapid, active drug release fast, role cycle is short, small side effect on normal cell, has huge application potential, simple reaction steps, the operation procedure is clear, and the molecular Image probe with anticancer prodrug combination, by the reasonable designed structure, is able to realize tumor target detection, can also realize the effect of targeting for the treatment of tumor, while at the same time monitoring prodrugs in vivo biodistribution, and active release of the medicament and the enrichment process, to study the mechanism of action of drugs, tumor drug resistance mechanism is of great significance. (by machine translation)

Access to Versatile β-Cyclodextrin Scaffolds through Guest-Mediated Monoacylation

Vurgun, Nesrin,G?mez-Biagi, Rodolfo F.,Nitz, Mark

supporting information, p. 1062 - 1069 (2016/01/16)

Herein, we report the selective mono-derivatization of heptakis[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD (1) through a guest-mediated covalent capture strategy. The use of guests functionalized with cleavable linkers enables the installation of an amine-orthogonal thiol group on the primary rim of 1 as a handle for further transformations to the β-CD scaffold. Applying this methodology, two novel monoderivatized β-CDs were obtained in good yield and high purity. Both of these monoacylated CDs were amenable to facile linker cleavage and further modification at the resulting thiol group. This methodology can be applied towards the synthesis heterofunctionalized β-CD constructs for analyte sensing, drug delivery, and other applications.

Bioreducible Poly- l -Lysine-Poly[HPMA] Block Copolymers Obtained by RAFT-Polymerization as Efficient Polyplex-Transfection Reagents

Tappertzhofen, Kristof,Beck, Simone,Montermann, Evelyn,Huesmann, David,Barz, Matthias,Koynov, Kaloian,Bros, Matthias,Zentel, Rudolf

, p. 106 - 120 (2016/01/25)

Polylysine-b-p[HPMA] block copolymers containing a redox-responsive disulfide bond between both blocks are synthesized by RAFT polymerization of pentafluorphenyl-methacrylate with a macro-CTA from N∈-benzyloxycarbonyl (Cbz) protected polylysine

TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS

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Paragraph 0066-0067, (2014/11/11)

The invention relates to cleavable chemistry in general, and in particular, to tunable fluoresence using cleavable linkers present in fluorochrome-quencher conjugates.

A kinetic approach to characterize the electrostatic environments of thiol groups in proteins

Zhang, Hao,Le, Min,Means, Gary E.

, p. 356 - 364 (2007/10/03)

In this study, we synthesized a zwitterionic DTNB derivative, 5-(2- aminoethyl)-dithio-2-nitrobenzoate (ADNB), and characterized its reactions with several cationic, anionic, and neutral thiols. Reactions with ADNB, unlike those with DTNB, are relatively insensitive to electrostatic environments and ionic strengths. At relatively low ionic strength, rate ratios, k(ADNB)/k(DTNB), varied from 0.22 for reactions with low-molecular- weight cationic thiols to 3.0 for those with low-molecular-weight anionic thiols. A k(ADNB)/k(DTNB) ratio of ~200 for Cys-34 of BSA appears to reflect a very anionic environment. k(ADNB)/k(DTNB) ratios of ~6 and ~1, respectively, for canine and equine serum albumins, which have Glu-82 → Asp and Glu-82 → Ala substitutions suggest Glu-82 is the most important anionic residues affecting the reactivity of Cys-34 in BSA. k(ADNB)/k(DTNB) ratios appear to be useful for characterizing electrostatic environments of thiol groups in proteins.

Design and synthesis of a bifunctional label for selection of β-lactamase displayed on filamentous bacteriophage by catalytic activity

Marchand-Brynaert, Jacqueline,Bouchet, Michele,Touillaux, Roland,Beauve, Cecile,Fastrez, Jacques

, p. 5591 - 5606 (2007/10/03)

A bifunctional activity label 1c has been constructed for the selection of active β-lactamases displayed on filamentous bacteriophage. It features an original 6-sulfonylamido-penam sulfone moiety, as β-lactamase suicide-inhibitor, and a biotinyl residue, for separation by affinity chromatography, connected through a linker including a cleavable disulfide bond. The inhibitor 28 resulted from coupling of methoxymethyl 6-aminopenicillinate 8 with N-protected (aminoethoxy)ethoxyethanesulfonyl chloride 23, followed by oxidation into the corresponding sulfone 25, and usual deprotections. The biotinyl ester 32 reacted with 3-(2-aminoethyldithio)propanoic acid 31 as linker, to give 33 which was further activated as pentafluorophenol ester 34b. Final coupling of the building blocks 28 and 34b gave the target label 1c.

Effect of Charged Substituents on Rates of the Thiol-Disulfide Interchange Reaction

Hupe, D. J.,Wu, Dorothy

, p. 3100 - 3103 (2007/10/02)

Rate constants in aqueous solution at 25 deg C are reported for the production of p-nitrothiophenol from the mixed disulfides RSSC6H4NO2 upon reaction with the thiol anions R'S-.The R' groups used varied in charge and include -O2CCH2CH2, +H3NCH2CH2, and HOCH2CH2.The R groups used were these same three in addition to -O2CCH2CH2CH2.The solutions of RSSC6H4NO2 were prepared by allowing O2NC6H4S- to react with an excess of RSSR, followed by rapidly mixing R'S- and measuring the return of the absorption due to O2NC6H4S-.The rates for reactions involvingcharged R and R' groups differ from those with uncharged groups of identical pKa by factors of up to 2.5.Negatively charged groups, especially on the central thiol, slow the reaction and positively charged groups speed the reaction to a greater extent than that predicted by the calibrating ionization reaction.Ramifications of these observations are considered for the prediction of rate constants of thiol-disulfide interchange reactions and for the interpretation of β values when reactants of various charge types are used.

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