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670359

Sigma-Aldrich

乙酰基硫甲基-硼烷二苯基膦复合物

≥98.0%

别名:

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

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About This Item

经验公式（希尔记法）:
C15H18BOPS
CAS号:
446822-71-5
分子量:
288.15
分類程式碼代碼:
12352200
PubChem物質ID:
329760266
NACRES:
NA.22

化驗

≥98.0%

形狀

solid

反應適用性

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

mp

52-55 °C

官能基

phosphine

儲存溫度

2-8°C

SMILES 字串

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

InChI 密鑰

MXPNVFCCEGQGEN-UHFFFAOYSA-N

應用

  • 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

包裝

Bottomless glass bottle. Contents are inside inserted fused cone.

法律資訊

授权后方可销售，仅供研发使用。美国专利 6,974,884 和相关专利申请

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说明
价格

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險聲明

H315,H319,H335

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves

从最新的版本中选择一种：

分析证书(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

商品

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.

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.

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