Fmoc-Trp(Boc)-OH

Fmoc-Trp(Boc)-OH

Conjugation of drug to poly(D,L-lactic-co-glycolic acid) for controlled release from biodegradable microspheres.[Pubmed:9895414]

J Control Release. 1999 Feb 22;57(3):269-80.

Poly(d,l-lactic-co-glycolic acid) (PLGA) was chemically conjugated to a model drug, N-(9-fluorenylmethoxycarbonyl-N-tert-butoxycarbonyl-l-tryptophan (Fmoc-Trp(Boc)) via an ester linkage. Various coupling reaction conditions were tested to optimize the conjugation process between a hydroxyl terminal group of PLGA and a carboxylic acid group of Fmoc-Trp(Boc). Two different lactic/glycolic acid compositions of PLGA (50/50 and 75/25) were used for the conjugation. The Fmoc-Trp(Boc)-PLGA conjugates were formulated into microspheres by a solvent evaporation technique for controlled release of Fmoc-Trp(Boc) over an one month period. A linear constant release of Fmoc-Trp(Boc) and its water-soluble PLGA oligomer conjugates was observed over an extended period without any initial burst effect, while unconjugated Fmoc-Trp(Boc) encapsulated within microspheres exhibited a rapid release profile. In addition, Fmoc-Trp(Boc) release rate solely depended on the PLGA composition that affected polymer degradation rate. The release rate of Fmoc-Trp(Boc) conjugated with fast degrading 50/50 PLGA was more rapid than that conjugated with relatively slow degrading 75/25 PLGA. This study demonstrates that PLGA-drug conjugation approach is a new and novel strategy to control the drug release rate from PLGA microspheres by utilizing the chemical degradation rate of PLGA backbone.

Nanoparticles generated from a tryptophan derivative: physical characterization and anti-cancer drug delivery.[Pubmed:28283907]

Amino Acids. 2017 May;49(5):975-993.

Surging reports of peptide-based nanosystems and their growing potency in terms of biological utility demand for the search of newer and simpler peptide-based systems that could serve as smart templates for the development of self-assembled nanostructures. Use of simple amino acids as monomeric building blocks for synthesizing ensembles of nanostructures have gained momentum in this direction with some reports focusing on the development of nanosystems from single or modified single amino acids. In this work, we have demonstrated self-assembly and nanoparticle formation ability of a single amino acid derivative, N-alpha-(9-fluorenylmethyloxycarbonyl)-N(in)-tert-butyloxycarbonyl-L-tryptophan [Fmoc-Trp(Boc)-OH]. The nanoparticles formed by the amino acid were found to be stable to various environmental perturbations like temperature, salts and showed responsiveness to pH change. These were capable of loading and releasing different bioactive molecules and were biocompatible. These systems demonstrated high cellular uptake and doxorubicin-loaded nanoparticles were found to be more efficient in killing glioma cells as compared to the drug alone. Thus, their simple amino acid-based origin along with the ability to ferry bioactive molecules to various cells, endows them the suitability for future applications in the field of drug delivery.

Differentiation of chiral phosphorus enantiomers by P and H NMR spectroscopy using amino acid derivatives as chemical solvating agents.[Pubmed:18037983]

Tetrahedron Asymmetry. 2007 Jul 4;18(12):1391-1397.

The ability of commercially available amino acid derivatives, especially Fmoc-Trp(Boc)-OH, to differentiate enantiomers of chiral phosphonates, phosphinates, phosphates, phosphine oxides, and phosphonamidates is demonstrated with (31)P, (13)C, and (1)H NMR spectroscopy. The chiral differentiation provided a rapid and convenient method for measuring the enantiomeric purity of these phosphorus compounds.