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

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

Uses

Used in Pharmaceutical Industry:
N-Cbz-L-Leucine is used as a reactant for the preparation of peptide-based potential antitumor agents. It plays a crucial role in the synthesis of peptides that have the potential to target and inhibit the growth of cancer cells.
Used in Chemical Synthesis:
N-Cbz-L-Leucine is used as a reactant for the preparation of cyclopropyl peptidomimetics. These peptidomimetics are synthetic compounds that mimic the structure and function of natural peptides, and they have potential applications in various fields, including drug discovery and development.
Used in Peptide Synthesis:
N-Cbz-L-Leucine is used as a building block in the synthesis of peptides. Its benzyloxycarbonyl protection group allows for the selective synthesis of complex peptide sequences, facilitating the development of novel therapeutic agents and other bioactive compounds.

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 
• 501-53-1 benzyl chloroformate 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 3242-70-4 Z-Leu-NHNHPh 
• 7324-05-2 L-alanine amide 
• 15893-47-7 (R)-2-amino-4-methylpentanamide 
• 687-51-4 H-L-Leu-NH₂ 
• 5241-58-7 L-Phenylalanine amide 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 7647-01-0 hydrogenchloride 
• 51021-87-5 N-benzyloxycarbonyl-L-leucine methyl ester 
• 19506-72-0 benzyl-8-quinolyl carbonate 
• 328-39-2 LEUCINE 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 

Downstream Products

• 104944-21-0 Z-S-Leu-R-Phe-OH 
• 16679-86-0 Z-L-Leu-D-Phe-OMe 
• 121969-80-0 [5']adenylic acid-(N-benzyloxycarbonyl-L-isoleucine)-anhydride 
• 1803-59-4 N-benzyloxycarbonyl-L-leucyl-L-alanine methyl ester 
• 4817-98-5 Z-Leu-Ile-OMe 
• 71730-80-8 Z-L-Leu-D-Leu-OMe 
• 3504-37-8 Cbz-L-Leu-L-Leu-OMe 
• 2419-37-6 H-Leu-N₂H₂-Boc 
• 16257-39-9 O-(N-Z-L-Leu)-pivalohydroxamsaeure 
• 33457-79-3 Z-Leu-O₃NP 
• 4801-68-7 O-(N-Benzyloxycarbonyl-L-leucyl)-N,N-dimethyl-hydroxylamin 
• 6401-56-5 tert-butyl (N-benzyloxycarbonyl-(S)-leucyl)glycinate 
• 33514-63-5 Z-Leu-Ser(Bu-t)-OMe 
• 1738-89-2 Benzyloxycarbonyl-L-leucyl-glycin-benzylester 

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.

SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides

Herein, the sulfonyl fluoro isocyanides were first developed as a new type of SuFExable synthon, and they are used as building blocks in the Ugi reaction (U-4CR). The Ugi reaction was established and the substrate scope was investigated, and various sulfonyl fluoro α-amino amides and peptides could be reached in a one-step synthesis. Therefore, this protocol opens a new vision for SuFExable building blocks and click chemistry, and it also provides a distinct approach to sulfonyl fluoro peptides.

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.

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

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.

Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts

The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.

Expanding the chemical space of anti-HCV NS5A inhibitors by stereochemical exchange and peptidomimetic approaches

Here we report a series of potent anti-HCV agents bearing a symmetrical benzidine l-prolinamide backbone with different capping groups including alkyl/aryl carbamates of natural and unnatural valine and leucine amino acids. All compounds were investigated for their inhibitory activity in an HCV replicon assay on genotype 1b. The novel compounds share some chemical and clinical attributes of commercially available NS5A inhibitors. Compounds 5 and 6 with unnatural capping residue and ethyl and isobutyl carbamates showed EC50 values in the picomolar range with a low toxicity profile and selectivity indices of several orders of magnitude. These findings enlarge the chemical space from which NS5A inhibitors may be discovered by adopting unnatural amino acids, amino acids other than valine and carbamates other than methyl as the capping groups.

Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors

On the basis of the application of proline-boronic acid as pharmacophore in the kinase inhibitors and our previous research results, using proline-boronic acid as warhead, two series of peptide proline-boronic acids, dipeptide proline-boronic acids (I) and tripeptide proline-boronic acids (II), were designed and synthesized. All the synthesized compounds were first evaluated for their biological activity against MGC803 cell, and then, the best compound II-7 was selected to test its anti-tumor spectrum on six human tumor cell lines and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors.

Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy

A novel 4-aminoquinoline derivative [(S)-7-chloro-N-(4-methyl-1-(4-methyl-piperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation

Novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation were developed; some of them possess Ki values in the micromolar range. We studied the structure-activity relationship of these derivatives and we performed docking studies, which allowed us to find out the key interactions established by the inhibitors with the target enzyme. Biological results indicate that the nature of the P2 and P3 substituents and their binding to the S2/S3 pockets is strictly interdependent.