Fmoc-Phe-OH-[15N]
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-Phe-OH-[15N]

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

Fmoc-Phe-OH-[15N] is the labelled analogue of L-Phenylalanine-N-FMOC. Phenylalanine is an α-amino acid essential for humans that is found in breast milk of mammals. It is commonly used as a dietary supplement.

Category
Fmoc-Amino Acids
Catalog number
BAT-005344
CAS number
125700-32-5
Molecular Formula
C24H21[15N]O4
Molecular Weight
388.42
Fmoc-Phe-OH-[15N]
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonyl(15N)amino)-3-phenylpropanoic acid
Synonyms
N-(9-Fluorenylmethoxycarbonyl)-L-phenylalanine-15N; L-Phenylalanine-15N N-Fmoc; Fmoc-[15N]Phe-OH; (((9H-Fluoren-9-yl)methoxy)carbonyl)-L-phenylalanine-15N
Related CAS
35661-40-6 (unlabelled)
Purity
99% (CP); 98% atom 15N
Density
1.328 g/cm3
Melting Point
180-187 °C
Boiling Point
322 °C at 760 mmHg
Storage
Store at -20°C
InChI
InChI=1S/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)/t22-/m0/s1/i25+1
InChI Key
SJVFAHZPLIXNDH-LJSUXKQBSA-N
Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1.Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction.
Kofoed J1, Nielsen J, Reymond JL. Bioorg Med Chem Lett. 2003 Aug 4;13(15):2445-7.
A series of oligo-peptide based catalysts were prepared using Fmoc solid-phase peptide synthesis. It was found that peptides with N-terminal proline residues catalyzed an aldol reaction yielding enantiomeric enriched product. Peptide H-Pro-Glu-Leu-Phe-OH catalyzed the reaction with good activity and moderate enantioselectivity (66% ee). Furthermore, it was shown that an acidic side chain and/or C-termini are essential to catalysis.
2.N-urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides.
Sureshbabu VV1, Naik SA, Hemantha HP, Narendra N, Das U, Guru Row TN. J Org Chem. 2009 Aug 7;74(15):5260-6. doi: 10.1021/jo900675s.
Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
3.Early detection of mycobacteria using a novel hydrogel culture method.
Jang MH1, Kim SY1, Kim CK2, Hwang SH3, Park BK4, Kim SS5, Lee EY1, Chang CL6. Ann Lab Med. 2014 Jan;34(1):26-30. doi: 10.3343/alm.2014.34.1.26. Epub 2013 Dec 6.
BACKGROUND: Early laboratory detection of Mycobacterium tuberculosis is crucial for controlling tuberculosis. We developed a hydrogel mycobacterial culture method that retains the advantages of both solid and liquid methods in terms of speed, cost, and efficiency.
4.Effect of C-terminal modification on the self-assembly and hydrogelation of fluorinated Fmoc-Phe derivatives.
Ryan DM1, Doran TM, Anderson SB, Nilsson BL. Langmuir. 2011 Apr 5;27(7):4029-39. doi: 10.1021/la1048375. Epub 2011 Mar 14.
The development of hydrogels resulting from the self-assembly of low molecular weight (LMW) hydrogelators is a rapidly expanding area of study. Fluorenylmethoxycarbonyl (Fmoc) protected aromatic amino acids derived from phenylalanine (Phe) have been shown to be highly effective LMW hydrogelators. It has been found that side chain functionalization of Fmoc-Phe exerts a significant effect on the self-assembly and hydrogelation behavior of these molecules; fluorinated derivatives, including pentafluorophenylalanine (F(5)-Phe) and 3-F-phenylalanine (3-F-Phe), spontaneously self-assemble into fibrils that form a hydrogel network upon dissolution into water. In this study, Fmoc-F(5)-Phe-OH and Fmoc-3-F-Phe-OH were used to characterize the role of the C-terminal carboxylic acid on the self-assembly and hydrogelation of these derivatives. The C-terminal carboxylic acid moieties of Fmoc-F(5)-Phe-OH and Fmoc-3-F-Phe-OH were converted to C-terminal amide and methyl ester groups in order to perturb the hydrophobicity and hydrogen bond capacity of the C-terminus.
Online Inquiry
Verification code
Inquiry Basket