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8.52288

Fmoc-Phe(CF2PO3)-OH

≥90.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-Phe(CF2PO3)-OH, Fmoc-F 2Pmp-OH,Fmoc-L-p-(phosphono-difluoromethyl)phenylalanine

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About This Item

Empirical Formula (Hill Notation):
C25H22F2NO7P
CAS Number:
160751-44-0
Molecular Weight:
517.42
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD01317828
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Product Name

Fmoc-Phe(CF2PO3)-OH, Novabiochem®

Quality Level

200

product line

Novabiochem®

assay

≥90.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

FC(F)([P](=O)(O)O)c1ccc(cc1)C[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O

InChI

1S/C25H22F2NO7P/c26-25(27,36(32,33)34)16-11-9-15(10-12-16)13-22(23(29)30)28-24(31)35-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,28,31)(H,29,30)(H2,32,33,34)/t22-/m0/s1

InChI key

XKWYQNFAGUNPJV-QFIPXVFZSA-N

General description

Building block [1] for the introduction by Fmoc SPPS of the hydrolytically stable phosphotyrosine analog phosphonodifluoromethylphenylalanine (F2Pmp) [2]. The pKa of F2Pmp more closely resembles that of a phosphate group making it better analog than phosphonomethylphenylalanine.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Guide to Selection of Orthogonally -Protected Building Blocks for Fmoc SPPS

Literature references

[1] M. F. Gordeev, et al. (1994) Tetrahedron Lett., 35, 7585.
[2] T. R. Burke, Jr. (2006) Curr. Top. Med. Chem., 6, 1465.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 90.0 % (a/a)
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.1 %

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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