198544-60-4

Usage

Uses

Used in Biochemistry and Pharmaceutical Research:
FMOC-D-LEU-CL is used as a protecting group for the amino group during peptide synthesis, which is crucial for the production of synthetic peptides and small proteins. Its role in protecting the amino group ensures that the peptide bonds form correctly and that the desired peptide sequence is achieved.
Used in Drug Development:
In the pharmaceutical industry, FMOC-D-LEU-CL is utilized in the development of new drugs and pharmaceuticals. Its application in peptide synthesis is vital for creating potential therapeutic agents, as many drugs are peptide-based and require precise synthesis to be effective.
Overall, FMOC-D-LEU-CL is an essential component in the fields of biochemistry and pharmaceutical research, playing a significant role in the synthesis of peptides and the development of new drugs.

Upstream product

• 35661-60-0 N-(9-fluorenylmethoxycarbonyl)-D-leucine 

Downstream Products

• 264281-98-3 N-(2-phenylethyl)-N-(benzoyloxy)-N_α-Fmoc-D-leucinamide 
• 264282-01-1 N-(2-phenylethyl)-N-(hydroxy)-N_α-Fmoc-D-leucinamide 

Relevant academic research and scientific papers

Synthesis of N-(hydroxy)amide- and N-(hydroxy)thioamide-containing peptides

Methods developed with N-(benzoyloxy)amines and hydroxamic acids were used in the synthesis of N-(hydroxy)amide-containing pseudopeptides. Acylation of N-(benzoyloxy)phenethylamine with the acid chloride of N(α)- Fmoc-L-leucine provided a N(α)-Fmoc-N-(benzoyloxy)-L-leucinamide in 90% yield. Deprotection of the benzoyl group (using 10 vol % NH4OH/MeOH) provided the N(α)-Fmoc-N-(hydroxy)-L-leucinamide in 87% yield. In general, the appended Fmoc group allowed for further elaboration of the N-hydroxy-N- (alkyl)amides using classic peptide-coupling methods. A practical synthetic strategy was developed, and racemization issues were addressed using diastereomeric Val-Leu derivatives. In addition, N-(hydroxy)thioamides were generated from the corresponding N-(benzoyloxy)thioamides. N- (Benzoyloxy)thioamides were obtained in moderate yields (53-76%) from the reaction of the corresponding N-(benzoyloxy)amides with Lawesson's reagent (i.e., 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide). In summary, this new technology allows for the introduction of either N- hydroxyamide or N-(hydroxy)thioamide linkages into pseudopeptide chains without racemization.