27527-05-5

Usage

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

• 60-18-4 L-tyrosine 
• 25341-42-8 (S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid 
• 5962-91-4 3-cyclohexyl-2-oxo-propionic acid 
• 701-97-3 cyclohexanepropionic acid 
• 119860-59-2 N-(Benzyloxycarbonyl)-2(S)-amino-3-cyclohexylpropionic acid 
• 7647-01-0 hydrogenchloride 
• 150-30-1 Phenylalanine 
• 63-91-2 L-phenylalanine 
• 3060-50-2 2,2-diphenylglycine 
• 3027-05-2 N,N'-diacetylpiperazin-2,5-dione 
• 2043-61-0 cyclohexanecarbaldehyde 
• 24371-94-6 cyclohexylmercury chloride 
• 626-62-0 Cyclohexyl iodide 
• 163085-09-4 (2S,4S)-4-(cyclohexylmethyl)-2-(1,1-dimethylethyl)-5-oxo-3-oxazolidinecarboxylic acid phenylmethyl ester 

Downstream Products

• 5962-91-4 3-cyclohexyl-2-oxo-propionic acid 
• 62377-41-7 (S)-3-cyclohexyl-2-hydroxypropionic acid 
• 81471-70-7 (S)-2-fluoro-3-cyclohexylpropionic acid 
• 126773-90-8 2(S)-(N,N-dibenzylamino)-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 
• 119601-26-2 morpholinocarbonylhexahydro-L-phenylalanine 
• 257296-61-0 (-)-N-((2S,3S)-3-hydroxy-1-cyclohexyl-4-pentenyl)benzamide 
• 858102-54-2 3-cyclohexyl-2-[(methanesulfonyliminomethylsulfanylmethyl)amino]propionic acid 
• 40056-18-6 methyl L-cyclohexylalaninate 
• 302-72-7 rac-Ala-OH 

Relevant academic research and scientific papers

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.

A general asymmetric synthesis of artificial aliphatic and perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling reaction

Aliphatic artificial α-amino acids (α-AAs) have attracted great interest in biochemistry and pharmacy. In this context, we developed a promising practical protocol for the asymmetric synthesis of these α-AAs through the selective and efficient intermolecular cross-electrophile coupling of Belokon's chiral dehydroalanine Ni(ii) complex with different alkyl and perfluoroalkyl iodides mediated by a dual Zn/Cu system. The reaction afforded diastereomeric complexes with dr up to 21.3?:?1 in 24-95% yields (19 examples). Exemplarily, three enantiomerically pure aliphatic α-AAs were obtained through acidic decomposition of (S,S)-diastereomers of Ni(ii) complexes. Importantly, the chiral auxiliary ligand (S)-BPB((S)-2-(N-benzylprolyl)aminobenzophenone) was easily recycled by simple filtration after acidic complex decomposition and reused for the synthesis of the initial dehydroalanine Ni(ii) complex.

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.

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.

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.

Ruthenium-catalyzed hydrogenation of aromatic amino acids in aqueous solution

A catalyst containing metallic ruthenium nanoparticles intercalated in hectorite (nanoRu@hectorite) was found to catalyze the hydrogenation of aromatic amino acids in aqueous solution. Thus, l-phenylalanine and l-phenylglycine can be converted exclusively into the corresponding l-cyclohexyl amino acids with retention of chirality under mild conditions (60 °C, 40 bar), conversion and selectivity being superior to 99%. The catalyst can be recycled and reused at least three times without loss in activity and selectivity.

SYNTHESIS METHOD FOR L-CYCLIC ALKYL AMINO ACID AND PHARMACEUTICAL COMPOSITION HAVING THEREOF

A synthesis method for L-cyclic alkyl amino acid and a pharmaceutical composition having the said amino acid are provide in the present disclosure provides. The synthesis method comprises: step A.) preparing a cyclic alkyl keto acid or a cyclic alkyl keto acid salt having Structural Formula (I) or Structural Formula (II), and step B.) mixing the cyclic alkyl keto acid or the cyclic alkyl keto acid salt with ammonium formate, a leucine dehydrogenase, a formate dehydrogenase and a coenzyme NAD+, and carrying out a reductive amination reaction to generate the L-cyclic alkyl amino acid, wherein the Structural Formula (I) is where n1≧1, m1≧0 and the M1 is H or a monovalent cation; the Structural Formula (II) is where n2≧0, m2≧0, the M2 is H or a monovalent cation, an amino acid sequence of the leucine dehydrogenase is SEQ ID No.1.

Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof

The invention relates to a novel chiral open-chain pyridoxamine catalyst and a synthesis method and application thereof. The structural general formula of the pyridoxamine catalyst is shown in the specification, wherein R1, R2, R3 and R4 are one of hydrogen, C1-24 alkyl, C1-24 alkyl containing substituent groups, substances shown in the specification and halogen, the substituent groups on C1-24 alkyl are a substance shown in the specification or a substance shown in the specification or a substance shown in the specification or O-Rw or S-Rw' or halogen, and Rx, Rx', Ry, Ry', Ry'', Rz, Rz', Rw and Rw' are one of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, benzyl, (1-phenyl)ethyl, 1-naphthyl, 2-naphthyl and halogen. Compared with the prior art, the pyridoxamine catalyst can achieve rapid and efficient synthesis of chiral amino acid, the preparation raw materials are easy to obtain, reaction conditions are mild, cost is low, and when the novel chiral open-chain pyridoxamine catalyst is used for a transamination reaction, the conditions are mild, and the reaction is stable.

Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination

Enzymatic transamination is catalyzed by pyridoxal/pyridoxamine, and it involves remarkable cooperative catalysis of a Lys residue in the transaminase. Inspired by transaminases, we developed a class of axially chiral pyridoxamines 11 bearing a lateral amine arm. The pyridoxamines exhibited high catalytic activity and excellent enantioselectivity in asymmetric transamination of α-keto acids, to give various α-amino acids in 67-99% yields with 83-94% ee's. The lateral amine arm likely participates in cooperative catalysis as the Lys residue does in biological transamination and has an important impact on the transamination in terms of activity and enantioselectivity.