27527-05-5

Basic information

• Product Name: L-Cyclohexylalanine
• Synonyms: (S)-CYCLOHEXYLALANINE;3-CYCLOHEXYL-L-ALANINE HYDROCHLORIDE;3-CYCLOHEXYL-L-ALANINE HYDROCHLORIDE SALT;3-CYCLOHEXYL-L-ALANINE;2-AMINO-3-CYCLOHEXYLPROPANOIC ACID;H-CHA-OH;H-CHA-OH HCL;H-BETA-CYCLOHEXYL-ALA-OH HCL
• CAS NO: 27527-05-5
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• EINECS: 1308068-626-2
• Product Categories: chiral
• Mol File: 27527-05-5.mol
• Article Data: 33

Chemical Properties

• Melting Point: 322 °C
• Boiling Point: 307.147 °C at 760 mmHg
• Flash Point: 139.558 °C
• Appearance: /Solid
• Density: 1.076 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: Store at 0°C
• PKA: 2.33±0.10(Predicted)
• CAS DataBase Reference: L-Cyclohexylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cyclohexylalanine(27527-05-5)
• EPA Substance Registry System: L-Cyclohexylalanine(27527-05-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 27527-05-5(Hazardous Substances Data)

Usage

Description

L-Cyclohexylalanine, also known as (S)-(+)-Cyclohexylalanine, is an amino acid analog characterized by its white to light yellow crystal powder appearance. It possesses pharmacological effects and has been the subject of research due to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
L-Cyclohexylalanine is used as a precursor for the synthesis of derivatives with potent bactericidal activity. These derivatives are particularly effective against drug-resistant gram-positive pathogens, making them valuable in the development of new antibiotics to combat antibiotic-resistant bacteria.
Used in Diabetes Treatment:
L-Cyclohexylalanine is used as a dipeptidyl peptidase-IV (DPP-IV) inhibitor, which plays a crucial role in the treatment or prevention of diabetes. By inhibiting DPP-IV, it helps regulate blood sugar levels and can be a significant component in the development of anti-diabetic medications.

References

http://nizetlab.ucsd.edu/Publications/CombinatorialLibrary.pdf Duffy, Joseph L, et al. "Cyclohexylalanine derivatives as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes." CN, CN 1960990 A. 2007. Aarstad, K, T. L. Zimmer, and S. G. Laland. "The fidelity of gramicidin S synthetase." European Journal of Biochemistry 112.2(1980):335-338.

InChI:InChI=1/C9H17NO2/c1-7(9(11)12)10-8-5-3-2-4-6-8/h7-8,10H,2-6H2,1H3,(H,11,12)/t7-/m0/s1

Upstream product

• 70984-38-2 2-Amino-3-{4-[3-[4-(2-amino-2-carboxy-ethyl)-phenoxy]-5-((R)-amino-carboxy-methyl)-2-hydroxy-phenoxy]-phenyl}-propionic acid 
• 63-91-2 L-phenylalanine 
• 25400-54-8 3-cyclohexyl-D-lactic acid 
• 65644-36-2 3-cyclohexylpropane-1,2-diol 
• 63-91-2 L-phenylalanine 
• 55065-02-6 2-(N-acetylamino)cinnamic acid 
• 204922-64-5 2-Benzyloxycarbonylamino-3-(1-nitro-cyclohexyl)-propionic acid methyl ester 
• 142035-71-0 2-Benzyloxycarbonylamino-3-cyclohexyl-propionic acid methyl ester 
• 2550-36-9 Cyclohexylmethyl bromide 
• 51692-88-7 3-cyclohexyl-2-oxopropionic acid ethyl ester 
• 5962-91-4 3-cyclohexyl-2-oxo-propionic acid 
• 7647-01-0 hydrogenchloride 
• 150-30-1 Phenylalanine 
• 119860-59-2 N-(Benzyloxycarbonyl)-2(S)-amino-3-cyclohexylpropionic acid 

Downstream Products

• 100400-96-2 (S)-2-acetylamino-3-cyclohexylpropionic acid 
• 131288-67-0 (2S)-2-amino-3-cyclohexyl-1-propanol 
• 264887-81-2 (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-3-cyclohexylpropanoic acid 
• 60025-25-4 (S)-2-amino-3-cyclohexyl-propionic acid ethyl ester; hydrochloride 
• 1361131-80-7 C₂₅H₃₅NO₃ 
• 1361131-89-6 C₂₆H₃₄ClNO₃ 
• 1361131-93-2 C₂₆H₃₆ClNO₃ 
• 1361131-63-6 C₂₆H₃₅NO₃ 
• 1361131-83-0 C₂₅H₂₇NO₃ 
• 1416992-34-1 benzyl ((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-(2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)carbamate 
• 40203-89-2 β-cyclohexyl-L-alanine methyl ester isocyanate 

Relevant articles and documents

Micropeptins 88-A to 88-F, chymotrypsin inhibitors from the cyanobacterium Microcystis aeruginosa (NIES-88)

Micropeptins 88-A to 88-F (1-6) have been isolated from the cyanobacterium Microcystis aeruginosa (NIES-88). Their structures were determined by two-dimensional 1H-1H and 1H-13C NMR correlation experiments and c

Synthesis method of L-tertiary leucine and L-cyclohexyl alanine

The invention discloses a synthesis method of L-tertiary leucine and L-cyclohexyl alanine, and belongs to the technical field of amino acid preparation. The method comprises the following steps: taking pentafluorophenol-(dibenzylamine) ester 1 and benzhydrol 2 as reactants, carrying out dynamic kinetic resolution reaction under the catalysis of chiral PPY nitrogen oxygen 3 to obtain a compound 4, and then carrying out Pd/C catalytic hydrogenation debenzylation to obtain L-tertiary leucine and L-cyclohexyl alanine. The oxygen atom in pyridine nitrogen oxygen in the chiral PPY nitrogen oxygen catalyst is used as a nucleophilic site to participate in dynamic kinetic resolution. The method has the advantages of being good in yield, high in enantioselectivity and the like, the ee of the obtained product can reach 99.5% or above, and a new path is provided for synthesis of chiral amino acid.

Immunoproteasome Inhibitor-Doxorubicin Conjugates Target Multiple Myeloma Cells and Release Doxorubicin upon Low-Dose Photon Irradiation

Proteasome inhibitors are established therapeutic agents for the treatment of hematological cancers, as are anthracyclines such as doxorubicin. We here present a new drug targeting approach that combines both drug classes into a single molecule. Doxorubicin was conjugated to an immunoproteasome-selective inhibitor via light-cleavable linkers, yielding peptide epoxyketone-doxorubicin prodrugs that remained selective and active toward immunoproteasomes. Upon cellular uptake and immunoproteasome inhibition, doxorubicin is released from the immunoproteasome inhibitor through photoirradiation. Multiple myeloma cells in this way take a double hit: immunoproteasome inhibition and doxorubicin-induced toxicity. Our strategy, which entails targeting of a cytotoxic agent, through a covalent enzyme inhibitor that is detrimental to tumor tissue in its own right, may find use in the search for improved anticancer drugs.

Enantioselective biomimetic transamination of α-keto acids catalyzed by H4-naphthalene-derived axially chiral biaryl pyridoxamines

Asymmetric biomimetic transamination is a highly attractive method for synthesis of chemically and biologically important chiral amino acids and chiral amines. Development of chiral pyridoxamines/pyridoxals is the key for the reaction. New axially chiral biaryl pyridoxamines based on H4-naphathene skeleton have been developed. The pyridoxamines display good enantioselectivity and high catalytic activity in asymmetric biomimetic transamination of α-keto acids, affording various optically active unnatural amino acids in 61–98% yields with up to 91% ee's.