N-β-(9-Fluorenylmethoxycarbonyl)-2,3,4,5,6-pentafluoro-D-β-homophenylalanine
Need Assistance?
  • US & Canada:
    +
  • UK: +

N-β-(9-Fluorenylmethoxycarbonyl)-2,3,4,5,6-pentafluoro-D-β-homophenylalanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Fluorinated amino acids
Catalog number
BAT-005525
CAS number
269398-94-9
Molecular Formula
C25H18F5NO4
Molecular Weight
491.41
N-β-(9-Fluorenylmethoxycarbonyl)-2,3,4,5,6-pentafluoro-D-β-homophenylalanine
IUPAC Name
(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2,3,4,5,6-pentafluorophenyl)butanoic acid
Synonyms
Fmoc-D-Phe(F5)-(C#CH2)OH; (R)-3-[(9-Fluorenylmethoxycarbonyl)amino]-4-(2,3,4,5,6-pentafluorophenyl)butanoic acid; FMOC-(R)-3-AMINO-4-(PENTAFLUORO-PHENYL)-butyric acid; Fmoc-D-b-HoPhe(F)5-OH; N-(9-FLUORENYLMETHOXYCARBONYL)-(R)-3-AMINO-4-(PENTAFLUOROPHENYL)BUTANOIC ACID; Fmoc-pentafluoro-D-β-homophenylalanine; Fmoc-D-β-HomoPhe(F)5-OH
Appearance
White powder
Purity
≥ 98%
Density
1.441±0.060 g/cm3
Boiling Point
616.7±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H18F5NO4/c26-20-17(21(27)23(29)24(30)22(20)28)9-12(10-19(32)33)31-25(34)35-11-18-15-7-3-1-5-13(15)14-6-2-4-8-16(14)18/h1-8,12,18H,9-11H2,(H,31,34)(H,32,33)/t12-/m1/s1
InChI Key
HCBMYXPXBOUBBR-GFCCVEGCSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=C(C(=C(C(=C4F)F)F)F)F)CC(=O)O
1.Qualitative/quantitative strategy for the determination of glufosinate and metabolites in plants.
Rojano-Delgado AM, Priego-Capote F, De Prado R, de Castro MD. Anal Bioanal Chem. 2014 Jan;406(2):611-20. doi: 10.1007/s00216-013-7484-y.
A simple method for the simultaneous determination of glufosinate and itsmetabolites in plants based on liquid chromatography–ultraviolet (LC–UV) absorption detection after derivatization with fluorenylmethoxycarbonyl chloride (FMOC-Cl) of some analytes to facilitate separation is reported here. Nonavailable standard metabolites were identified by LC–TOF/mass spectrometry (MS), which also confirmed all target analytes. Ultrasound-assisted extraction was used for sample preparation (power of 70 Wand duty cycle of 0.7 s/s for 10 min) with subsequent evaporation of the extractant, reconstitution and filtration as the cleanup/concentration step prior to derivatization, and chromatographic separation and detection at 270 nm for underivatized analytes and 340 nm for those that were derivatized. The chromatographic analysis was completed in 40 min using a Luna® column (C18 phase). The analytical characteristics of the method were linear dynamic range of the calibration curves within 0.
2.Synthesis of diastereomerically pure Lys(Nε-lipoyl) building blocks and their use in Fmoc/tBu solid phase synthesis of lipoyl-containing peptides for diagnosis of primary biliary cirrhosis.
Rentier C1, Pacini G, Nuti F, Peroni E, Rovero P, Papini AM. J Pept Sci. 2015 May;21(5):408-14. doi: 10.1002/psc.2761. Epub 2015 Mar 26.
Primary Biliary Cirrhosis is an immune-mediated disease in which one of the epitopes recognized by antimitochondrial autoantibodies is a lipoylated fragment of the PDC-E2 protein. Accordingly, the synthesis of lipoylated peptides as diagnostic tools is a relevant target. Up to now, the proper tools for the introduction of lipoylation on building blocks to be used in Fmoc/tBu solid phase peptide synthesis (SPPS) are lacking, and the role of chirality in lipoylation remains poorly studied. In this paper, we present the synthesis of lipoylated lysine derivatives as pure diastereomeric building blocks suitable for Fmoc/tBu SPPS and their introduction in relevant peptide sequences to possibly serve as synthetic probes for the development of novel diagnostic tools for this disease. The optimization of the synthesis of lipoylated building blocks derived from racemic, (R)-, and (S)-α-lipoic acid is described. Synthesis of peptide probes incorporating lipoylation is described.
3.Conformation and crystal structures of 1-amino-cyclo-hexa-neacetic acid (β(3,3)Ac6c) in N-protected derivatives.
Ahmad Wani N1, Gupta VK2, Kant R2, Aravinda S1, Rai R1. Acta Crystallogr Sect E Struct Rep Online. 2014 Oct 4;70(Pt 11):272-7. doi: 10.1107/S1600536814020777. eCollection 2014.
N-Protected derivatives of 1-amino-cyclo-hexa-neacetic acid (β(3,3)-Ac6c), namely Valeroyl-β(3,3)-Ac6c-OH [2-(1-pentanamidocyclohexyl)acetic acid, C13H23NO3], (I), Fmoc-β(3,3)-Ac6c-OH [2-(1-{[(9H-fluoren-9-yloxy)carbonyl]amino}cyclohexyl)acetic acid, C23H25NO4], (II), and Pyr-β(3,3)-Ac6c-OH {2-[1-(pyrazine-2-amido)cyclohexyl]acetic acid, C13H17N3O3}, (III), were synthesized and their conformational properties were determined by X-ray diffraction analysis. The backbone torsion angles (ϕ, θ) for β(3,3)-Ac6c-OH are restricted to gauche conformations in all the derivatives, with a chair conformation of the cyclo-hexane ring. In the crystal structure of (I), the packing of mol-ecules shows both carb-oxy-lic acid R 2 (2)(8) O-H⋯O and centrosymmetric R (2) 2(14) N-H⋯O hydrogen-bonding inter-actions, giving rise to chains along the c-axis direction. In (II), centrosymmetric carb-oxy-lic acid R 2 (2)(8) O-H⋯O dimers are extended through N-H⋯O hydrogen bonds and together with inter-ring π-π inter-actions between Fmoc groups [ring centroid distance = 3.
4.Stereospecific electrophoretically mediated microanalysis assay for methionine sulfoxide reductase enzymes.
Zhu Q1, El-Mergawy RG, Heinemann SH, Schönherr R, Jáč P, Scriba GK. Anal Bioanal Chem. 2014 Feb;406(6):1723-9. doi: 10.1007/s00216-013-7596-4. Epub 2014 Jan 15.
An electrophoretically mediated microanalysis assay (EMMA) for the determination of the stereoselective reduction of L-methionine sulfoxide diastereomers by methionine sulfoxide reductase enzymes was developed using fluorenylmethyloxycarbonyl (Fmoc)-L-methionine sulfoxide as substrate. The separation of the diastereomers of Fmoc-L-methionine sulfoxide and the product Fmoc-L-methionine was achieved in a successive multiple ionic-polymer layer-coated capillary using a 50 mM Tris buffer, pH 8.0, containing 30 mM sodium dodecyl sulfate as background electrolyte and an applied voltage of 25 kV. 4-Aminobenzoic acid was employed as internal standard. An injection sequence of incubation buffer, enzyme, substrate, enzyme, and incubation buffer was selected. The assay was optimized with regard to mixing time and mixing voltage and subsequently applied for the analysis of stereoselective reduction of Fmoc-L-methionine-(S)-sulfoxide by human methionine sulfoxide reductase A and of the Fmoc-L-methionine-(R)-sulfoxide by human methionine sulfoxide reductase B.
Online Inquiry
Verification code
Inquiry Basket