33900-15-1

Basic information

• Product Name: L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-
• CAS NO: 33900-15-1
• Molecular Formula: C20H31N3O4
• Molecular Weight: 377.484
• Mol File: 33900-15-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 83-85 °C
• Boiling Point: 615.6±55.0 °C(Predicted)
• Density: 1.108±0.06 g/cm3(Predicted)
• CAS DataBase Reference: L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-(33900-15-1)
• EPA Substance Registry System: L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-(33900-15-1)

Safety Data

• Hazardous Substances Data: 33900-15-1(Hazardous Substances Data)

Usage

Uses

N-[(1,1-Dimethylethoxy)carbonyl]-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).

Upstream product

• 3392-09-4 Boc-Leu-ONSu 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 63-91-2 L-phenylalanine 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 5241-58-7 L-Phenylalanine amide 
• 33900-00-4 (S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid pyridin-2-yl ester 
• 63096-02-6 N-tert-butoxycarbonyl-L-leucine methyl ester 

Downstream Products

• 38678-60-3 leucylphenylalanylamide 
• 74214-38-3 L-leucyl-L-phenylalaninamide hydrochloride 
• 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 
• 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 
• 292632-98-5 (5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide 
• 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 
• 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 
• 294675-33-5 Boc-Leu-gPhe-COOMe 
• 109121-33-7 <4(S)--2,2-difluoro-3(R)-hydroxy-6-methyheptanoyl>-L-leucyl-L-phenylalaninamide 
• 109064-95-1 <4(S)--2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-leucyl-L-phenylalaninamide 
• 109064-97-3 <4(S)-amino-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-leucyl-L-phenylalaninamide trifluoroacetate 
• 87063-27-2 Boc-Phe-His-Sta-Leu-Phe-NH₂ 
• 98168-94-6 His-Sta-Leu-Phe-NH₂*2HCl 
• 87063-45-4 Ac-Phe-His-Sta-Leu-Phe-NH₂ 

Relevant articles and documents

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-

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.

Renin Inhibitors. Syntheses of Subnanomolar, Competitive, Transition-State Analogue Inhibitors Containing a Novel Analogue of Statine

Analogues of the renin octapeptide substrate were synthesized in which replacement of the scissile dipeptide with (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine, Sta) transformed the substrate sequence into potent, transition-state analogue, competitive inhibitors of renin.Synthesis and incorporation of the cyclohexylalanyl analogue of Sta, (3s,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA), gave the most potent inhibitors of renin yet reported, including N-isovaleryl-L-histydyl-L-prolyl-L-phenylalanyl-L-histydyl-ACHPA-L-leucyl-L-phenylalanyl amide , with renin inhibitions of Ki=1.6 * 10-10 M (human kidney renin), IC50=1.7 * 10-10 M (human plasma renin), IC50=1.9 * 10-9 M (dog plasma renin), and IC50=2.1 * 10-8 M (rat plasma renin).This inhibitor 3, containing ACHPA, was 55-76 times more potent vs. human renin than the comparable Sta-containing inhibitor 1 and 17 times more potent vs. dog renin than 1.Inhibitor 3 lowered blood pressure in sodium-deficient dogs, with in vivo potency 19 times that shown by 1, in close agreement with the relative in vitro potencies.Structure-activity results are presented that show the minimal N-terminus for these inhibitors.An ACHPA-containing pentapeptide, N--L-phenylalanyl-L-histydyl-ACHPA-L-lecyl-L-phenylalanyl amide , retained subnanomolar inhibitory potency.Molecular modelling studies are described that suggested the design of ACHPA.