38678-60-3

Usage

Uses

Used in Pharmaceutical Industry:
Leucyl-phenylalanine amide is used as an intermediate in the synthesis of γ-Secretase Inhibitors for the treatment of Alzheimer's disease (AD). These inhibitors target the enzyme complex responsible for the cleavage of amyloid precursor protein (APP), which generates amyloid β-peptide (Aβ). Aβ is the primary causative agent in the development of AD, and thus, Leucyl-phenylalanine amide plays a crucial role in the development of therapeutic strategies against this debilitating condition.
Additionally, Leucyl-phenylalanine amide may also be utilized in other applications within the pharmaceutical industry, such as the development of novel drug delivery systems or as a component in the synthesis of other therapeutic agents. Its specific use would depend on the ongoing research and development efforts in the field.

InChI:InChI=1/C15H23N3O2/c1-10(2)8-12(16)15(20)18-13(14(17)19)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H2,17,19)(H,18,20)/t12-,13-/m0/s1

Upstream product

• 5241-58-7 L-Phenylalanine amide 
• 94580-89-9 N-benzyloxycarbonyl-L-leucine 2,4,6-trichlorophenyl ester 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 35661-60-0 Fmoc-Leu-OH 
• 35661-40-6 N-Fmoc L-Phe 
• 3392-09-4 Boc-Leu-ONSu 
• 63-91-2 L-phenylalanine 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 33900-15-1 (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[(tert-butoxycarbonyl)amino]-4-methylpentanamide 

Downstream Products

• 1427084-77-2 Ac-Leu-Ser(tBu)-Lys(Boc)-Gln(Trt)-Met-Leu-Phe-NH₂ 
• 1449018-13-6 Cbz-Leu-Phe-Leu-Phe-NH₂ 
• 1449018-19-2 Cbz-Leu-Ala-Leu-Phe-NH₂ 
• 1427084-71-6 Cbz-Ala-Leu-Phe-Leu-Phe-NH₂ 
• 1138243-26-1 bis(Boc-Cys-Leu-Phe-NH₂) 
• 98818-74-7 L-364,505 
• 292620-20-3 (1S,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-oxo-5-phenylpentyl}carbamic acid tert-butyl ester 
• 292632-98-5 (5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide 
• 126409-24-3 {(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester 
• 338801-69-7 {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester 
• 126410-32-0 {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Discovery of dipeptides with high affinity to the specific binding site for substance P1-7

Substance P 1-7 (SP1-7, H-Arg-Pro-Lys-Pro-Gln-Gln-Phe-OH) is the major bioactive metabolite of substance P. The interest in this heptapeptide originates from the observation that it modulates, and in certain cases opposes the effects of the parent peptide, e.g., the nociceptive effect. The μ-opioid receptor agonist endomorphin-2 (EM-2, H-Tyr-Pro-Phe-Phe-NH2) has been found to also interact with the specific binding site of SP 1-7 with only a 10-fold lower affinity compared to the native peptide. Considering the smaller size of EM-2 compared to the target heptapeptide, it was selected as a lead compound in the development of low-molecular-weight ligands to the SP1-7 binding site. An alanine scan and truncation study led to the unexpected discovery of the dipeptide H-Phe-Phe-NH2 (Ki = 1.5 nM), having equal affinity as the endogenous heptapeptide SP1-7. Moreover, the studies show that the C-terminal phenylalanine amide is crucial for the affinity of the dipeptide.

Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458

The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-

Short total synthesis of aspartyl protease inhibitors L-685,434, L-682,679 and L-685,458

Hydroxyethylene dipeptide isosteres L-685,434, L-682,679 and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-aminoaldehyde followed by hydroboration of the corresponding 1,2-syn and 1,2-anti a

Design and synthesis of HIV protease inhibitors. Variations of the carboxy terminus of the HIV protease inhibitor L-682,679

A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.

DESIGN AND SYNTHESIS OF A MULTI-DETACHABLE BENZHYDRYLAMINE-RESIN FOR SOLID PHASE PEPTIDE SYNTHESIS

Peptides with C-terminal α-carboxamides were synthesized from a multi-detachable benzhydrylamine-resin containing a Boc-(4-acetoxy)benzhydrylamine handle of unambiguous origin.The peptides bound to the new resin are stable to trifluoroacetic acid, but are cleavable by hydrogen fluoride, base and nucleophiles to give unprotected or protected peptide fragments.