77426-98-3

Usage

Uses

Used in Pharmaceutical Industry:
L-Leucine, N-[N-(N-glycylglycyl)-L-phenylalanyl]-, 1,1-dimethylethyl ester is used as a pharmaceutical compound for its potential biological activities. It may contribute to the development of new drugs and therapies due to its unique structure and properties.
Used in Research Laboratories:
In research settings, L-Leucine, N-[N-(N-glycylglycyl)-L-phenylalanyl]-, 1,1-dimethylethyl ester is utilized for studying peptide chemistry and exploring its potential applications in various biological processes.
Used in Drug Delivery Systems Development:
L-Leucine, N-[N-(N-glycylglycyl)-L-phenylalanyl]-, 1,1-dimethylethyl ester is employed in the development of novel drug delivery systems. Its unique structure allows for the design of targeted and efficient drug delivery platforms, improving the efficacy and safety of therapeutic agents.
Used in Biotechnology:
In the field of biotechnology, L-Leucine, N-[N-(N-glycylglycyl)-L-phenylalanyl]-, 1,1-dimethylethyl ester may have potential applications as a building block for the synthesis of peptides and proteins. Its incorporation into biotechnological processes could lead to the creation of new bioactive molecules with specific functions.
Used in Peptide and Protein Synthesis:
As a building block, L-Leucine, N-[N-(N-glycylglycyl)-L-phenylalanyl]-, 1,1-dimethylethyl ester is used in the synthesis of peptides and proteins. Its unique properties may enable the development of new peptide-based drugs and therapeutic agents with enhanced efficacy and selectivity.

Upstream product

• 89137-25-7 (S)-2-((S)-2-{2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetylamino]-acetylamino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid tert-butyl ester 
• 28635-78-1 L-phenylalanyl-L-leucine tert-butyl ester 
• 63-91-2 L-phenylalanine 
• 122236-89-9 DC-FM-bar-Phe-OH 
• 122269-91-4 DC-FM-bar-Gly-Phe-Leu-O-t-Bu 
• 122237-16-5 DC-FM-bar-Phe-Leu-O-t-Bu 
• 84891-01-0 Fmoc-Phe-Leu-OtBu 
• 82362-19-4 Gly-Phe-Leu(t-Bu) 
• 2748-02-9 L-leucine tert-butyl ester hydrochloride 
• 35661-40-6 N-Fmoc L-Phe 
• 93962-35-7 (S)-2-((S)-2-{2-[2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-acetylamino]-acetylamino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid tert-butyl ester 
• 122269-92-5 DC-FM-bar-Gly-Gly-Phe-Leu-O-t-Bu 
• 149204-99-9 Fmoc-Gly-L-Phe-L-Leu-OtBu 

Downstream Products

• 138372-38-0 Fmoc-Tyr(OBu^t)-Gly-Gly-Phe-Leu-OBu^t 
• 101493-45-2 hZ-Tyr(Bn)-Gly-Gly-Phe-Leu-O-t-Bu 
• 81678-16-2 leucine enkephalin acetate 
• 427881-22-9 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-tert-butoxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 136484-94-1 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 73563-78-7 L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-leucine trifluoroacetate 
• 58822-25-6 Leu-enkephalin 
• 123168-00-3 (S)-2-[(S)-2-(2-{2-[(S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 122269-93-6 DC-FM-bar-Tyr(t-Bu)-Gly-Gly-Phe-Leu-O-t-Bu 

Relevant academic research and scientific papers

A new method for rapid solution synthesis of shorter peptides by use of PyBOP

By using PyBOP promoted coupling of Fmoc protected amino acids, and adopting the deprotection/washing procedure of the Fmoc Amino Acid Chloride Solution Technique (FAACST), a sample of [leucine5] enkephalin has been synthesized in a rapid, cont

Investigation of the Reaction between Amino Acids or Amino Acid Esters and 9-Formylfluorene and Its Equivalents. Possible Utility of the Derived Enamines as Amino Group Protectants

Treatment of 9-(hydroxymethylene)fluorene/9-formylfluorene (storable as the hemiacetal with methanol, 7) with amino acids and amino acid esters yields the corresponding enamines 8, which may be considered to be hydrocarbon analogues of N-formyl amino acid derivatives.Attempted coupling of the free acids 8 (R'=H) with amino acid esters failed, suggesting insufficient reduction in basicity of the amino group due to the enamine residue.The introduction of electron-withdrawing substituents into the fluorene ring decreases the basicity sufficiently to allow normal peptide coupling reactions, as for example with the 2,7-dichloro analogues derived from 17.Thus phenylalanine derivative 18 treated with leucine methyl ester and DCC gave dipeptide 19.The DC-FM-bar group could be removed by catalytic transfer hydrogenolysis.Mild acid hydrolysis represents a second general deblocking technique for the FM-bar function.It was demonstrated in a model study involving the highly sensitive amino acid α-phenylglycine that the FM-bar protecting group was less prone to cause racemization than the benzyloxycarbonyl function.It was demonstrated that the simple pentapeptide leucine enkephalin 29 could be synthesized using α-DC-FM-bar protection along with tert-butyl-based side chain protecting groups.

Thioxanthene Dioxide Based Amino-Protecting Groups Sensitive to Pyridine Bases and Dipolar Aprotic Solvents

In pursuit of an analogy between fluorine and thioxanthene dioxide, the suitability of the D-TMOC and related functions as base-sensitive amino-protecting groups was examined.Such compounds were found to be cleaved by mild pyridine bases against which the analogous FMOC derivatives are stable.Deblocking gives as a byproduct the methylene sulfone 5 or its adducts with an appropriate secondary deblocking amine.Certain solvents such as DMSO, DMF, etc., were also found to deblock the D-TMOC group, especially on warming, whereas the compounds were stable in ordinary nonpolar solvents (e.g., CH2Cl2, benzene, THF).For practical use the D-TMOC function suffers from excessive solvent sensitivity and the low solubility of some derivatives.To overcome this problem tert-butyl groups were introduced into the 2,7-positions of the xanthene nucleus.The resulting DBD-TMOC function proved easier to handle in terms of both solubility and reactivity.The key alcohol 12 was synthesized from diphenyl sulfide 13 by tert-butylation followed by Friedel-Crafts cyclization using methyl dichloromethyl ether to give a 50-50 mixture of thioxanthene 15 and corresponding thioxanthone 16.Without separation of the mixture, oxidation gave a mixture of the dioxides 17 and 18, and again without separation the mixture was reduced by P/HI to give the desired compound 17 in an overall yield of 60-65percent.Formylation of 17 followed by reduction gave 12, from which urethanes 11 were obtained in the normal manner via the chloroformate.The DBD-TMOC group was stable to strong acids (TFA, HBr-HOAc) but deblocked by catalytic hydrogenolysis as well as via mild bases and warming in dipolar aprotic solvents.Upon deblocking of 11 in DMSO the byproduct 27 separated completely, especially if 3-5percent water is present or added subsequently.This process provides a clean solution of the deblocked amine, thus simplifying the use of the DBD-TMOC function in peptide synthesis.An example given is that of leucine enkephalin, in which all coupling steps were effected by acid chlorides and all deblocking steps by warming in DMSO.It was shown with model compounds that coupling could be effected under appropriate conditions without racemization.