Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

653152

Sigma-Aldrich

4-Mercaptophenylacetic acid

97%

Synonym(s):

(4-Carboxymethyl)thiophenol, (4-Sulfanylphenyl)acetic acid, 2-(4-Mercaptophenyl)acetic acid, 2-(4-Sulfanylphenyl)acetic acid, 4-Mercaptobenzeneacetic acid, p-Mercaptophenylacetic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
HSC6H4CH2CO2H
CAS Number:
39161-84-7
Molecular Weight:
168.21
MDL number:
MFCD00797617
UNSPSC Code:
12352100
PubChem Substance ID:
24883931
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

105-109 °C (lit.)

functional group

carboxylic acid

storage temp.

2-8°C

SMILES string

OC(=O)Cc1ccc(S)cc1

InChI

1S/C8H8O2S/c9-8(10)5-6-1-3-7(11)4-2-6/h1-4,11H,5H2,(H,9,10)

InChI key

ORXSLDYRYTVAPC-UHFFFAOYSA-N

General description

4-Mercaptophenylacetic acid (MPAA), a thiol additive, is widely used in Native Chemical Ligation (NCL) reactions for selective and efficient ligation of peptide fragments.

Application

4-Mercaptophenylacetic acid has been used in the preparation of small ubiquitin-like modifier peptides from bis(2-sulfanylethyl)amido peptide via sequential native chemical ligation.
It can be used:
  • On-resin preparation of peptide-α thiophenylesters which are used in a chemical ligation process for the chemical synthesis of peptides.
  • In one pot deprotection of (acetamido-methyl)cysteine following native chemical ligation and/or desulfurization method for the preparation of peptides.
  • Palladium facilitated deprotection of N-terminal cysteine through native chemical ligation method for the preparation of synthetically challenging proteins.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ8150
MKCM9940
MKCJ9065
MKCG4136
MKCF2365

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Sunithi Gunasekera et al.
Frontiers in microbiology, 11, 168-168 (2020-03-11)
Can antimicrobial activity and peptide stability of alpha-helical peptides be increased by making them into dimers and macrocycles? Here, we explore that concept by using KR-12 as the starting point for peptide engineering. KR-12 has previously been determined as the
Lin Zhang et al.
Chemical science, 10(11), 3271-3280 (2019-04-19)
Targeted antibody blocking enables characterization of binding sites on immunoglobulin G (IgG), and can efficiently eliminate harmful antibodies from organisms. In this report, we present a novel peptide-denoted as a dual-functional conjugate of antigenic peptide and Fc-III mimetics (DCAF)-for targeted
Palladium mediated rapid deprotection of N-terminal cysteine under native chemical ligation conditions for the efficient preparation of synthetically challenging proteins
Jbara M, et al.
Journal of the American Chemical Society, 138(15), 5069-5075 (2016)
One-pot chemical synthesis of small ubiquitin-like modifier protein-peptide conjugates using bis (2-sulfanylethyl) amido peptide latent thioester surrogates
Boll E, et al.
Nature Protocols, 10(2), 269-269 (2015)
Daniel J Capon et al.
Proceedings of the Japan Academy. Series B, Physical and biological sciences, 87(9), 603-616 (2011-11-15)
There is a significant need for antibodies that can bind targets with greater affinity. Here we describe a novel strategy employing chemical semisynthesis to produce symmetroadhesins: antibody-like molecules having nonprotein hinge regions that are more flexible and extendible and are
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service