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Merck
CN

653152

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

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About This Item

Linear Formula:
HSC6H4CH2CO2H
CAS Number:
39161-84-7
Molecular Weight:
168.21
NACRES:
NA.22
PubChem Substance ID:
24883931
UNSPSC Code:
12352100
MDL number:
MFCD00797617
Assay:
97%
Form:
solid

Key Documents

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InChI

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

SMILES string

OC(=O)Cc1ccc(S)cc1

InChI key

ORXSLDYRYTVAPC-UHFFFAOYSA-N

assay

97%

form

solid

mp

105-109 °C (lit.)

functional group

carboxylic acid

storage temp.

2-8°C

Quality Level

100

Related Categories

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX0024
MKCT0499
MKCS7237
MKCR1774
MKCQ8150

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Efficient palladium-assisted one-pot deprotection of (acetamidomethyl) cysteine following native chemical ligation and/or desulfurization to expedite chemical protein synthesis
Maity SK, et al.
Angewandte Chemie (International Edition in English), 55(28), 8108-8112 (2016)
Direct on-resin synthesis of peptide-αthiophenylesters for use in native chemical ligation
Bang D, et al.
Organic Letters, 8(6), 1049-1052 (2006)
Jailson Brito Querido et al.
Science (New York, N.Y.), 369(6508), 1220-1227 (2020-09-05)
A key step in translational initiation is the recruitment of the 43S preinitiation complex by the cap-binding complex [eukaryotic initiation factor 4F (eIF4F)] at the 5' end of messenger RNA (mRNA) to form the 48S initiation complex (i.e., the 48S).
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
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)
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