38678-60-3

Basic information

• Product Name: leucyl-phenylalanine amide
• Synonyms: leucyl-phenylalanine amide;L-Leucyl-L-phenylalaninaMide;(2S)-2-amino-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-4-methylpentanamide
• CAS NO: 38678-60-3
• Molecular Formula: C₁₅H₂₃N₃O₂
• Molecular Weight: 277.362
• Mol File: 38678-60-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 538.8°Cat760mmHg
• Flash Point: 279.7°C
• Appearance: /
• Density: 1.112g/cm³
• Vapor Pressure: 1.11E-11mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: Refrigerator
• Solubility: DCM, Hexane
• CAS DataBase Reference: leucyl-phenylalanine amide(CAS DataBase Reference)
• NIST Chemistry Reference: leucyl-phenylalanine amide(38678-60-3)
• EPA Substance Registry System: leucyl-phenylalanine amide(38678-60-3)

Safety Data

• Hazardous Substances Data: 38678-60-3(Hazardous Substances Data)

Usage

Uses

L-Leucyl-L-phenylalaninamide is an intermediate in the synthesis of γ-Secretase Inhibitor, the enzyme complex that catalyzes the cleavage of the amyloid precursor protein (APP) to generate amyloid β-peptide (Aβ), the major causative agent in Alzheimer disease (AD).

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

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

Downstream Products

• 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 
• 292632-98-5 (5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide 
• 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 
• 1138243-26-1 bis(Boc-Cys-Leu-Phe-NH₂) 
• 1449018-19-2 Cbz-Leu-Ala-Leu-Phe-NH₂ 
• 1449018-13-6 Cbz-Leu-Phe-Leu-Phe-NH₂ 
• 1427084-77-2 Ac-Leu-Ser(tBu)-Lys(Boc)-Gln(Trt)-Met-Leu-Phe-NH₂ 
• 1427084-71-6 Cbz-Ala-Leu-Phe-Leu-Phe-NH₂ 
• 98818-74-7 L-364,505 
• 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 articles and documents

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.

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 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.