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670359

Sigma-Aldrich

Acetylthiomethyl-diphenylphosphine borane complex

≥98.0%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C15H18BOPS
Numero CAS:
446822-71-5
Peso molecolare:
288.15
Codice UNSPSC:
12352200
ID PubChem:
329760266
NACRES:
NA.22

Saggio

≥98.0%

Forma fisica

solid

Impiego in reazioni chimiche

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

Punto di fusione

52-55 °C

Gruppo funzionale

phosphine

Temperatura di conservazione

2-8°C

Stringa SMILE

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
MXPNVFCCEGQGEN-UHFFFAOYSA-N

Applicazioni

  • 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

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Note legali

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

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCBG5052V
1409638V
1409638
1355729

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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

Articoli

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.

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

Contatta l'Assistenza Tecnica.