Fmoc protected phenylalanine

Manufactured by Merck Group

Sourced in Germany

Fmoc-protected phenylalanine is a chemical compound used in the synthesis of peptides and proteins. It consists of the amino acid phenylalanine with a Fmoc (fluorenylmethyloxycarbonyl) protecting group attached to the amino terminus. This compound is commonly used as a building block in solid-phase peptide synthesis and other applications requiring the controlled incorporation of phenylalanine residues.

Automatically generated - may contain errors

Lab products found in correlation

Tentagel r ram, by Rapp Polymere (1 mentions)

Spelling variants of this product

Phenylalanine (126 citations)

2 protocols using fmoc protected phenylalanine

Esterification of Iodinated Boron Dipyrromethene Compound

Check if the same lab product or an alternative is used in the 5 most similar protocols

Example 6

Prepared according to the general procedure for esterification reaction from 11 as shown below:

[Figure (not displayed)]

Compound 11 (49 mg, 0.08 mmol), phenylacetic acid (22 mg, 0.16 mmol), DCC (38 mg, 0.19 mmol) and DMAP (1 mg, 0.008 mmol) in dry dichloromethane (5 mL); reaction time: 4 h. Compound 6 was purified by flash chromatography (dichloromethane). Dark purple solid. Yield 36 mg (87%). Mp. 94-98° C. ¹H NMR (400 MHz, CDCl₃) δ (ppm): 7.38-7.07 (m, 5H, 5CH), 5.35 (s, 2H, CH₂), 3.70 (s, 2H, CH₂), 2.55 (s, 6H, 2CH₃), 2.28 (s, 6H, 2CH₃), 0.21 (s, 6H, 2CH₃). ¹³C NMR (100 MHz, CDCl₃) δ (ppm): 171.34 (C), 153.94 (C), 139.60 (C), 133.31 (C), 132.52 (C), 131.16 (C), 129.31 (CH), 128.91 (CH), 127.63 (CH), 87.72 (CH), 59.62 (CH₂), 41.26 (CH₂), 18.57 (CH₃), 18.31 (CH₃). HRMS-ESI [M−1]⁻ calcd for C₂₄H₂₆BI₂N₂O₂638.0218, found 638.0228.

Example 7

Compound 7, having the formula:

[Figure (not displayed)]
Can be synthesized using a procedure similar to the one described for compound 6, in Example 6, except that the phenylacetic acid is replaced with Fmoc-protected phenylalanine available from Sigma-Aldrich.

US10493153B2. Alkylated photoremovable protecting groups and uses thereof (2019-12-03). Iowa State University Research Foundation, Inc. [US]. Inventors: Arthur Henry Winter [US].

+ Open protocol

+ Expand

Isotopically Labeled Peptide Synthesis

Check if the same lab product or an alternative is used in the 5 most similar protocols

¹³C₉,¹⁵N₁-labeled phenylalanine (Sigma-Aldrich GmbH, Taufkirchen, Germany) was Fmoc-protected using standard procedures [19 (link)]. Subsequently, the peptide synthesis of the Pep19-2.5 derivative containing four ¹³C₉,¹⁵N₁-labeled phenylalanine residues (analyte, Figure 3) was carried out by standard manual Fmoc/tBu solid-phase peptide synthesis on Fmoc-Rink amide resin (TentaGel R RAM, Rapp Polymere GmbH, Tübingen, Germany) [20 (link)]. The Fmoc-protected L-amino acids were purchased from ORPEGEN Peptide Chemicals GmbH (Heidelberg, Germany). For coupling of the isotope-labeled amino acid, 2 equivalents and a coupling time of 2.5 h was used.
The synthesis of deuterated Pep19-2.5 was carried out on an automated synthesizer (433A, Applied Biosystems, Waltham, MA, USA) on Fmoc-Rink amide resin. For the synthesis of the Pep19-25 derivative containing 32 deuterium atoms, eightfold deuterated Fmoc-protected phenylalanine (Sigma Aldrich, GmbH, Taufkirchen, Germany) was used and applied in excess of two equivalents. Pep19-2.5 labeled with ¹⁴C was obtained from Rainer Bartels (Leibniz-Zentrum für Medizin und Biowissenschaften, Borstel, Germany).

Wohlfart S., Kilian M., Storck P., Gutsmann T., Brandenburg K, & Mier W. (2021). Mass Spectrometric Quantification of the Antimicrobial Peptide Pep19-2.5 with Stable Isotope Labeling and Acidic Hydrolysis. Pharmaceutics, 13(9), 1342.

+ Open protocol

+ Expand

About PubCompare

Our mission is to provide scientists with the largest repository of trustworthy protocols and intelligent analytical tools, thereby offering them extensive information to design robust protocols aimed at minimizing the risk of failures.

We believe that the most crucial aspect is to grant scientists access to a wide range of reliable sources and new useful tools that surpass human capabilities.

However, we trust in allowing scientists to determine how to construct their own protocols based on this information, as they are the experts in their field.

Ready to get started?

Revolutionizing how scientists
search and build protocols!