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Merck
CN

29208

(N-Succinimidyloxycarbonylmethyl)tris(2,4,6-trimethoxyphenyl)phosphonium bromide

for protein sequence analysis (by MALDI-MS), 98%

Synonym(s):

N-Succinimidyl [tris(2,4,6-trimethoxyphenyl)phosphonio]acetate bromide, TMPP-Ac-OSu

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About This Item

Empirical Formula (Hill Notation):
C33H39BrNO13P
CAS Number:
226409-58-1
Molecular Weight:
768.54
MDL number:
MFCD03095505
UNSPSC Code:
41116105
PubChem Substance ID:
329753320
NACRES:
NA.21

Key Documents

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Quality Level

100

Assay

≥97.5% (HPLC)
98%

technique(s)

MALDI-MS: suitable

storage temp.

−20°C

SMILES string

[Br-].COc1cc(OC)c(c(OC)c1)[P+](CC(=O)ON2C(=O)CCC2=O)(c3c(OC)cc(OC)cc3OC)c4c(OC)cc(OC)cc4OC

InChI

1S/C33H39NO13P.BrH/c1-38-19-12-22(41-4)31(23(13-19)42-5)48(18-30(37)47-34-28(35)10-11-29(34)36,32-24(43-6)14-20(39-2)15-25(32)44-7)33-26(45-8)16-21(40-3)17-27(33)46-9;/h12-17H,10-11,18H2,1-9H3;1H/q+1;/p-1

InChI key

YKMSQZIYVKTUHI-UHFFFAOYSA-M

General description

N-Succinimidyloxycarbonylmethyl tris(2,4,6-trimethoxyphenyl)phosphonium bromide (TMPP-Ac-OSu) is an acylating reagent, and is generally used for the selective derivatization of N-terminal a-amino group of peptide. The TMPP-acetylated peptides undergo fragmentation thereby creating a-type ions, thus obtaining sequence information becomes easier, even without the usage of automated computational approach. It can be used as a labelling reagent in liquid chromatography-coupled mass spectrometry (LC-MS/MS) of N-terminal peptides, so as to improve ionization efficiency, simplify fragmentation, and retention times, thereby leading to better separation of peptides.

Application

TMPP-Ac-OSu was used for labelling peptides, in tandem mass spectrometry, done for converting arginine to ornithine, in order to improve the fragmentation pattern of peptides.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Reagent for modifying N-termial of peptides for fast atom bombardment, FAB or matrix assisted laser desorption/ionization MS, MALDI MS

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9858
BCCB9000
BCBP9987V

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Ortho-proteogenomics: multiple proteomes investigation through orthology and a new MS-based protocol.
Gallien S
Genome Research, 19 (1), 128-135 (2009)
Conversion of arginine to ornithine for improving the fragmentation pattern of peptides labeled with the N-terminal tris (2, 4, 6-trimethoxyphenyl) phosphonium group in tandem mass spectrometry.
Kuyama H
Analytical Methods : Advancing Methods and Applications, 2 (11), 1792-1797 (2010)
Z H Huang et al.
Analytical biochemistry, 268(2), 305-317 (1999-03-17)
We have recently reported a simple procedure by which low picomole quantities of peptides can be modified to the corresponding N-Tris(2, 4,6-trimethoxyphenyl)phosphonium-acetyl (TMPP-Ac) derivatives (Z. H Huang, J. Wu, D. A. Gage, and J. T. Watson, Anal. Chem. 69, 137-144
Z. Huang et al.
Analytical Biochemistry, 69, 137-137 (1997)
M Lisa Manier et al.
Journal of mass spectrometry : JMS, 49(8), 665-673 (2014-07-22)
Imaging mass spectrometry (IMS) studies increasingly focus on endogenous small molecular weight metabolites and consequently bring special analytical challenges. Since analytical tissue blanks do not exist for endogenous metabolites, careful consideration must be given to confirm molecular identity. Here, we

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