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670359

Sigma-Aldrich

Acetylthiomethyl-diphenylphosphin-Boran-Komplex

≥98.0%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C15H18BOPS
CAS-Nummer:
446822-71-5
Molekulargewicht:
288.15
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329760266
NACRES:
NA.22

Assay

≥98.0%

Form

solid

Eignung der Reaktion

reaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction

mp (Schmelzpunkt)

52-55 °C

Funktionelle Gruppe

phosphine

Lagertemp.

2-8°C

SMILES String

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

InChIKey

MXPNVFCCEGQGEN-UHFFFAOYSA-N

Anwendung

  • 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

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Rechtliche Hinweise

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

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Preisangaben

914487

2-(Diphenylphosphanyl)benzamide, ≥95%

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCBG5052V
1409638V
1409638
1355729

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Die Dokumentenbibliothek aufrufen

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

Artikel

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.

Protokolle

Traceless Staudinger Ligation

Traceless Staudinger Ligation

Verwandter Inhalt

Raines Group – Professor Product Portal

Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

Setzen Sie sich mit dem technischen Dienst in Verbindung.