2018-66-8

Basic information

• Product Name: N-Cbz-L-Leucine
• Synonyms: BENZYLOXYCARBONYL-L-LEUCINE;CBZ-L-LEU-OH;CBZ-L-LEUCINE;CBZ-LEUCINE;CBZ-LEU-OH;N-ALPHA-BENZYLOXYCARBONYL-L-LEUCINE;N-CARBOBENZOXY-L-LEUCINE;N-BENZYLOXYCARBONYL-L-LEUCINE
• CAS NO: 2018-66-8
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• EINECS: 217-960-3
• Product Categories: Amino Acid Derivatives;Leucine [Leu, L];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 2018-66-8.mol
• Article Data: 77

Chemical Properties

• Boiling Point: 408.52°C (rough estimate)
• Flash Point: 85 °F
• Appearance: /viscous liquid
• Density: 1 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.28E-08mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.00±0.21(Predicted)
• Water Solubility: Not miscible or difficult to mix in water. Soluble in chloroform, DMSO and methanol.
• BRN: 1253861
• CAS DataBase Reference: N-Cbz-L-Leucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-Leucine(2018-66-8)
• EPA Substance Registry System: N-Cbz-L-Leucine(2018-66-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/22-37/38-40-41-36/37/38-20/21/22-67-63-19
• Safety Statements: 16-26-36/37/39-45-36-36/37-60
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: OH2921000
• Hazardous Substances Data: 2018-66-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow oil or weak solid

Uses

Reactant for:Peptide-based preparation of potential antitumor agentsPreparation of cyclopropyl peptidomimeticsPeptide synthesis

Definition

ChEBI: A L-leucine derivative obtained by the substitution of a benzyloxycarbonyl group on the nitrogen atom.

InChI:InChI=1/C14H19NO4/c1-10(2)8-12(13(16)17)15-14(18)19-9-11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3,(H,15,18)(H,16,17)/t12-/m1/s1

Upstream product

• 61-90-5 L-leucine 
• 42116-21-2 2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine 
• 7324-05-2 L-alanine amide 
• 15893-47-7 (R)-2-amino-4-methylpentanamide 
• 687-51-4 H-L-Leu-NH₂ 
• 100-51-6 benzyl alcohol 
• 53363-87-4 N-(benzyloxycarbonyl)leucine dicyclohexylamine salt 
• 501-53-1 benzyl chloroformate 
• 328-39-2 LEUCINE 
• 26054-60-4 ((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester 
• 1068-55-9 isopropylmagnesium chloride 
• 3242-70-4 Z-Leu-NHNHPh 
• 920-36-5 (2-methylpropyl)lithium 
• 193091-62-2 (E)-(R)-O-(1-phenylbutyl)cinnamaldehyde oxime 

Downstream Products

• 104944-21-0 Z-S-Leu-R-Phe-OH 
• 16679-86-0 Z-L-Leu-D-Phe-OMe 
• 64187-29-7 Z-L-Leu-OCH₂CN 
• 33457-76-0 Z-Leu-OCP 
• 2706-38-9 N-(N-benzyloxycarbonyl-L-leucyl)-glycine 
• 5084-98-0 methyl N-benzyloxycarbonyl-L-leucylglicynate 
• 16881-37-1 (S)-tert-butyl 2-(benzyloxycarbonylamino)-4-methylpentanoate 
• 131066-55-2 methyl O-(N-carbobenzoxy-L-leucyl)hydroxyethanoate 
• 53481-48-4 (S)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoate 
• 131066-57-4 methyl O--(S)-2-hydroxypropanoate 
• 3504-37-8 Cbz-L-Leu-L-Leu-OMe 
• 4865-35-4 Bz-Glu-γ-OMe-Leu-OMe 
• 4817-99-6 Bz-Leu-Glu-γ-OMe-OMe 
• 27169-29-5 Bz-Glu-γ-OMe-Glu-γ-OMe-OMe 

Relevant articles and documents

Design and synthesis of novel symmetric fluorene-2,7-diamine derivatives as potent hepatitis C virus inhibitors

Hepatitis C virus (HCV) is an international challenge. Since the discovery of NS5A direct-acting antivirals, researchers turned their attention to pursue novel NS5A inhibitors with optimized design and structure. Herein we explore highly potent hepatitis C virus (HCV) NS5A inhibitors; the novel analogs share a common symmetrical prolinamide 2,7-diaminofluorene scaffold. Modification of the 2,7-diaminofluorene backbone included the use of (S)-prolinamide or its isostere (S,R)-piperidine-3-caboxamide, both bearing different amino acid residues with terminal carbamate groups. Compound 26 exhibited potent inhibitory activity against HCV genotype (GT) 1b (effective concentration (EC50) = 36 pM and a selectivity index of >2.78 × 106). Compound 26 showed high selectivity on GT 1b versus GT 4a. Interestingly, it showed a significant antiviral effect against GT 3a (EC50 = 1.2 nM). The structure-activity relationship (SAR) analysis revealed that picomolar inhibitory activity was attained with the use of S-prolinamide capped with R- isoleucine or R-phenylglycine residues bearing a terminal alkyl carbamate group.

PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS

Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.

Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ～1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.