What is Fmoc materials？

Description

The Fmoc group molecule, also known as 9-Fluorenylmethyloxycarbonyl, has a stable structure. It is a widely used reagent for a variety of chemical production and has become an important intermediate in drug synthesis because of its ability to protect amine groups. Due to its inherent hydrophobicity and aromatics, which promote hydrophobic and p-p stacking interactions, Fmoc-modi dipeptides have excellent self-assembly properties and can be used as excellent low molecular weight hydrogenators^[1].

Advantages of Fmoc materials

Fmoc materials include Fmoc-Glu(Otbu)-OH,Fmoc-lle-OH, and Fmoc-Phe-OH, among others.These Fmoc materials are more significant in bio-chemicals and pharmaceuticals because of their good stability, low molecular weight,low toxicity, minimal side effect, and amine group protecting properties^[2]. Moreover, self-assembled Fmoc variants can be used in supramolecular electronics, drug delivery vehicles, photonics, healing agents for regenerative drugs, cell culture, tissue engineering, and other bionanotechnology fields.

Fmoc-Phe-OH 

Fmoc-Phe-OH is white to light yellow crystal powde. Fmoc-Phe-OH used in the preparation of peptides and deltorphin derivatives. A potential inhibitor of IGF-I and IGF-Binding Protein-5 complex. In 2019, Dou et al. co-assembled Fmoc-Phe-OH and 4,4-azopyridine into photoresponsive supramolecular hydrogels. The material can control the increased amount of dye release by controlling the light exposure time^[3].

Fmoc-Glu (OtBu)-OH

Fmoc-L-glutamic acid 5-tert-butyl ester (Fmoc-Glu (OtBu)-OH) is a Fmoc derivative with an N-substituted tert‑butyl ester molecule. It belongs to Fmoc materials and therefore has many properties of Fmoc materials. At room temperature, Fmoc-Glu (OtBu)-OH is assembled into balls at both lower and higher concentrations. However, regardless of the concentration, it forms a broom stick-like form during the heating process^[4]. Fmoc-Glu (Otbu)-OH reacts effectively with a variety of organic compounds in the delivery system of a variety of diseases, including Alzheimers disease, tuberculosis, cancer, viruses and bacteria, and inflammation. In 2016, Gu et al. developed ligand-mediated prodrugs which specifically target cancer cells. This prodrug uses Fmoc-Glu (Otbu)-OH as a linker and transferrin as a carrier, combined with Paclitaxel. This prodrug called Tf–Glu–PTX. Compared with free PTX，Tf–Glu–PTX significantly decreased side effects and enhanced the antitumor efficiency^[5].

Based on the good properties of the materials, Fmoc materials are more significant in bio-chemicals and pharmaceuticals.

references

[1] K. Tao, E. Yoskovitz, L. Adler-Abramovicha, E. Gazit, Optical property modulation of Fmoc group by pHdependent self-assembly, RSC Advances, 2015, 5, 73914.

[2] M. Thirunavukkarasu, G. Balaji, P. Prabakaran, Shaik Jaheer Basha, Ahmad Irfan, S. Saleem Javed, S. Muthu, Spectral characterization, solvation effects on topological aspects, and biological attributes of Fmoc-L-glutamic acid 5‑tert‑butyl ester: An effective reagent in anticancer evaluations, Journal of Molecular Structure, 2022, 1269, 133793. 

[3] X. Dou, C. Zhao, N.a Mehwish, P. Li, C.g Feng, H.r Schönherr, Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release, Chinese Journal of Polymer Science, 2019, 37, 437–443. 

[4] N. Gour, B. Koshti, S. Naskar, V. Kshtriya, H. Narode, Controlled aggregation properties of modified single amino acids,ChemRxiv, 2021.

[5] L. Shan, X. Shan, T. Zhang, K. Zhai, G. Gao, X. Chenc, Y. Gu, Transferrin-conjugated paclitaxel prodrugs for targeted cancer therapy, RSC Advances, 2016, 6, 77987.

You may like