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653152

Sigma-Aldrich

4-Mercaptophenylacetic acid

97%

Sinônimo(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

Fórmula linear:
HSC6H4CH2CO2H
Número CAS:
39161-84-7
Peso molecular:
168.21
Número MDL:
MFCD00797617
Código UNSPSC:
12352100
ID de substância PubChem:
24883931
NACRES:
NA.22

Nível de qualidade

100

Ensaio

97%

forma

solid

pf

105-109 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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)

chave InChI

ORXSLDYRYTVAPC-UHFFFAOYSA-N

Descrição geral

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

Aplicação

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.

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Frases de perigo

H315,H318,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
MKCQ8150
MKCM9940
MKCJ9065
MKCG4136
MKCF2365

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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
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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
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