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670359

Sigma-Aldrich

Acetylthiomethyl-diphenylphosphine borane complex

≥98.0%

Synonyme(s) :

(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron

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About This Item

Formule empirique (notation de Hill):
C15H18BOPS
Numéro CAS:
446822-71-5
Poids moléculaire :
288.15
Code UNSPSC :
12352200
ID de substance PubChem :
329760266
Nomenclature NACRES :
NA.22

Pureté

≥98.0%

Forme

solid

Capacité de réaction

reaction type: click chemistry

Pertinence de la réaction

reagent type: ligand
reaction type: Staudinger Reaction

Pf

52-55 °C

Groupe fonctionnel

phosphine

Température de stockage

2-8°C

Chaîne SMILES 

B.CC(=O)SCP(c1ccccc1)c2ccccc2

InChI

1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3

Clé InChI

MXPNVFCCEGQGEN-UHFFFAOYSA-N

Application

  • Traceless Staudinger ligation reagent with borane protecting group.
  • The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.
  • After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.
  • Used in the synthesis of cyclic peptides.
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Informations légales

Sold under license for research and development purposes only. US Patent 6,974,884 and related patents apply

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315 - H319 - H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Matthew B Soellner et al.
The Journal of organic chemistry, 67(14), 4993-4996 (2002-07-06)
The Staudinger ligation of peptides with a C-terminal phosphinothioester and N-terminal azide is an emerging method in protein chemistry. Here, the first Staudinger ligations of nonglycyl azides are reported and shown to proceed both in nearly quantitative yield and with
Michaela Mühlberg et al.
Bioorganic & medicinal chemistry, 18(11), 3679-3686 (2010-05-15)
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the

Articles

Traceless Staudinger Ligation

Traceless Staudinger Ligation

Traceless Staudinger Ligation

Based on the same working principle as the nontraceless Staudinger Ligation the auxiliary phosphine reagent can be cleaved from the product after the ligation is completed leaving a native amide bond. Thus, the total chemical synthesis of proteins and glycopeptides is enabled overcoming the limitations of native chemical ligation (NCL) of a Cys residue at the ligation juncture.

Azide Building Blocks for Chemical Ligation

Chemoselective ligation strategies are a key success factor for chemical biology research. Ligation techniques open pathways to fully synthetic large peptides and even proteins.

Staudinger Ligation

The reaction between an azide and a phosphine forming an aza-ylide was discovered almost a century ago by Nobel Prize laureate Herrmann Staudinger.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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