Fmoc-L-F2Pmp-OH

Chemical name: 4-(Difluorophosphonomethyl)-N-(9-fluorenylmethyloxycarbonyl)-L-phenylalanine // Synonyms: Fmoc-L-Phe(4-CF2PO3)-OH, Fmoc-L-p-(Phosphono-difluoromethyl)phenylalanine, (2S)-3-[4-[Difluoro(phosphono)methyl]phenyl]-2-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)propanoic acid, 4-(Difluorophosphonomethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-Phenylalanine

Product code:FAA5595
CAS No.:160751-44-0
Formula:C25H22F2NO7P
Molecular weight:517.42 g/mol
Grouped product items
Qty Packing unit Price SKU
100 mg
$810.00
FAA5595.0100
250 mg
$1,620.00
FAA5595.0250
Safety Data Sheets
description

Hydrolysis-stable mimic of Phosphotyrosine; fluorination makes the phoshonic acid more acidic and thus a better mimic of phosphotyrosine than Pmp (compare to FAA1745 Fmoc-L-Pmp-OH and FAA5590 Fmoc-L-Pmp(OtBu)2-OH)


references

An Intrinsic Hydrophobicity Scale for Amino Acids and Its Application to Fluorinated Compounds; W. Hoffmann, J. Langenhan, S. Huhmann, J. Moschner, R. Chang, M. Accorsi, J. Seo, J. Rademann, G. Meijer, B. Koksch, M. T. Bowers, G. von Helden and K. Pagel; Angew Chem Int Ed Engl 2019; 58: 8216-8220. https://doi.org/10.1002/anie.201813954

Phosphatase-Stable Phosphoamino Acid Mimetics That Enhance Binding Affinities with the Polo-Box Domain of Polo-like Kinase 1; D. Hymel and T. R. Burke, Jr.; ChemMedChem 2017; 12: 202-206. https://doi.org/10.1002/cmdc.201600574

Cell-permeable bicyclic peptidyl inhibitors against T-cell protein tyrosine phosphatase from a combinatorial library; H. Liao and D. Pei; Org Biomol Chem 2017; 15: 9595-9598. https://doi.org/10.1039/c7ob02562a

Azide-alkyne cycloaddition-mediated cyclization of phosphonopeptides and their evaluation as PTP1B binders and enrichment tools; C. Meyer, B. Hoeger, J. Chatterjee and M. Kohn; Bioorg Med Chem 2015; 23: 2848-53. https://doi.org/10.1016/j.bmc.2015.03.015

Development of accessible peptidic tool compounds to study the phosphatase PTP1B in intact cells; C. Meyer, B. Hoeger, K. Temmerman, M. Tatarek-Nossol, V. Pogenberg, J. Bernhagen, M. Wilmanns, A. Kapurniotu and M. Kohn; ACS Chem Biol 2014; 9: 769-76. https://doi.org/10.1021/cb400903u

A highly selective and potent PTP-MEG2 inhibitor with therapeutic potential for type 2 diabetes; S. Zhang, S. Liu, R. Tao, D. Wei, L. Chen, W. Shen, Z. H. Yu, L. Wang, D. R. Jones, X. C. Dong and Z. Y. Zhang; J Am Chem Soc 2012; 134: 18116-24. https://doi.org/10.1021/ja308212y

Acquisition of a potent and selective TC-PTP inhibitor via a stepwise fluorophore-tagged combinatorial synthesis and screening strategy; S. Zhang, L. Chen, Y. Luo, A. Gunawan, D. S. Lawrence and Z. Y. Zhang; J Am Chem Soc 2009; 131: 13072-9. https://doi.org/10.1021/ja903733z

Cellular effects of small molecule PTP1B inhibitors on insulin signaling; L. Xie, S. Y. Lee, J. N. Andersen, S. Waters, K. Shen, X. L. Guo, N. P. Moller, J. M. Olefsky, D. S. Lawrence and Z. Y. Zhang; Biochemistry 2003; 42: 12792-804. https://doi.org/10.1021/bi035238p

Acquisition of a specific and potent PTP1B inhibitor from a novel combinatorial library and screening procedure; K. Shen, Y. F. Keng, L. Wu, X. L. Guo, D. S. Lawrence and Z. Y. Zhang; J Biol Chem 2001; 276: 47311-9. https://doi.org/10.1074/jbc.M106568200

Why is phosphonodifluoromethyl phenylalanine a more potent inhibitory moiety than phosphonomethyl phenylalanine toward protein-tyrosine phosphatases?; L. Chen, L. Wu, A. Otaka, M. S. Smyth, P. P. Roller, T. R. Burke, Jr., J. den Hertog and Z. Y. Zhang; Biochemical and biophysical research communications 1995; 216: 976-84. https://doi.org/10.1006/bbrc.1995.2716

Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F2Pmp; T. R. Burke, Jr., H. K. Kole and P. P. Roller; Biochemical and biophysical research communications 1994; 204: 129-34. https://doi.org/10.1006/bbrc.1994.2435


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