Name: 3-Mercaptopropionic acid NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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In stock

Solubility

In DMSO: 100 mg/mL (492.08 mM; Need ultrasonic)

Storage

Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

(2,5-dioxopyrrolidin-1-yl) 3-sulfanylpropanoate

InChI Key

UTBOEPMMEANMPS-UHFFFAOYSA-N

InChI

InChI=1S/C7H9NO4S/c9-5-1-2-6(10)8(5)12-7(11)3-4-13/h13H,1-4H2

SMILES

C1CC(=O)N(C1=O)OC(=O)CCS

1. Self-assembled monolayers as the coating in a quartz piezoelectric crystal immunosensor to detect Salmonella in aqueous solution

Y S Fung, Y Y Wong Anal Chem. 2001 Nov 1;73(21):5302-9. doi: 10.1021/ac010655y.

A new procedure based on the self-assembled monolayers (SAM) of alkanethiols was developed to immobilize antibodies onto gold electrodes of a quartz crystal microbalance (QCM) for detecting Salmonella paratyphi A. The procedure includes (1) chemisorption of 3-mercaptopropionic acid (MPA) at electrode surfaces to produce a carboxylic acid terminated monolayer, (2) activation by 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) and N-hydrosuccinimide (NHS) to generate a stable acyl amino ester intermediate, and (3) condensation of antibodies after aminolysis of the NHS adduct. Activation by two coupling agents (EDC and NHS) was shown to enhance the stability of the coating and facilitate the formation of a suitable intermediate to condense antibodies reproducibly and densely at the SAM, leading to high sensitivity and good precision of the developed immunosensor. With 50 min incubation under continuous monitoring, working ranges from 10(2) to 10(5) cells/mL with repeatability < 10% RSD were obtained. On the basis of S/N = 3, the detection limit was 1.7 x 10(2) cells/mL The MO2 piezoimmunosensor developed was specific to differentiate S. paratyphi A against Escherichia coli and other serogroups of Salmonella that are commonly present together.

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	4.9208 mL	24.6039 mL	49.2078 mL
5 mM	0.9842 mL	4.9208 mL	9.8416 mL
10 mM	0.4921 mL	2.4604 mL	4.9208 mL

3-Mercaptopropionic acid NHS ester, is designed to enable efficient formation of stable amide linkages between a carboxyl-functionalized targeting element and an NHS-activated partner. Its activated ester chemistry supports controlled conjugation under mild conditions, improving compatibility with sensitive ligands used in targeted protein degradation workflows. The sections below describe the linker’s structure and reactivity in detail.

Structure: The molecule contains an N-hydroxysuccinimide ester derived from a mercapto-substituted carboxylic acid. It features an activated carboxylate–NHS bond, a three-carbon spacer bearing a thiol functionality, and typical amide-forming ester reactivity. The presence of sulfur and the ester activation impart distinct polarity and conjugation behavior.

Reactivity: The NHS ester undergoes nucleophilic acyl substitution with primary amines to form amide bonds, releasing NHS as the leaving group. Conjugations are commonly performed in aqueous or mixed aqueous buffers at conditions that preserve NHS ester stability while maintaining amine nucleophilicity. Thiol-containing intermediates can be handled under reducing or thiol-compatible conditions to avoid unwanted oxidation, and reaction progress is typically monitored by analytical methods suitable for amide formation.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂