(3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

Base Information

• Chemical Name: (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate
• CAS No.: 49642-07-1
• Molecular Formula: C8H17NO3
• Molecular Weight: 175.228
• Hs Code.: 2922509090
• Mol file: 49642-07-1.mol

Synonyms:

Chemical Property of (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.83E-06mmHg at 25°C
• Melting Point: 209 °C
• Refractive Index: 1.49
• Boiling Point: 355.1 °C at 760 mmHg
• PKA: 3.97±0.10(Predicted)
• Flash Point: 168.5 °C
• PSA: 83.55000
• Density: 1.112 g/cm³
• LogP: 0.89570
• Storage Temp.: 2-8°C
• Solubility.: 0.5 M HCl: 50 mg/mL, clear, very faintly yellow
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 175.12084340
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

98%min ^*data from raw suppliers

STATINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(CC(=O)[O-])O)[NH3+]
• Isomeric SMILES: CC(C)C[C@@H]([C@H](CC(=O)[O-])O)[NH3+]
• Clinical Use: With the possible exception of atorvastatin, the statins are used to lower LDL cholesterol in familial or polygenic ( multifactorial) hypercholesterolemia (type IIa) and in combination with triglyceride-lowering drugs to treat combined hyperlipidemia (type IIb) when both LDL and VLDL (very low density lipoproteins) are elevated. However, the statins probably should not be given with the fibrates (triglyceridelowering drugs, discussed later), since this combination may greatly increase statin toxicity. Atorvastatin, the most potent of the available statins, has also been shown to lower blood triglycerides significantly. This effect may be due to decreasing hepatic cholesterol and cholesterol ester levels to such an extent that hepatic formation of VLDL is impaired.The statins also have been claimed to reduce blood cholesterol levels modestly in some patients with homozygous familial hypercholesterolemia, a condition often fatal in childhood or in early adulthood. The statins may lower the risk of CHD by decreasing inflammation, an important component of atherogenesis. Lovastatin decreased elevated plasma levels of Creactive protein, a marker for cellular inflammation, and acute coronary events in patients with relatively low plasma cholesterol levels. Recent studies also suggest that use of statins may decrease the risk of stroke, dementia, and Alzheimer’s disease and may improve bone density in postmenopausal women. These broad actions may be related to the hypocholesterolemic, antiproliferative, antiinflammatory, or antioxidant properties of the statins or some combination of these properties.

Technology Process of (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

There total 96 articles about (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

methyl (3S,4S)-3-hydroxy-6-methyl-4-(isopropoxycarbonyl)aminoheptanoate (128625-47-8) → statine (49642-07-1)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 100 ℃;

DOI:10.1016/S0040-4039(00)94374-0

Reference yield: 88.0%

(3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid (390377-64-7) → statine (49642-07-1)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In methanol; water; for 2h;

DOI:10.1016/S0040-4020(01)00804-3

Reference yield: 85.0%

(3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid (55714-49-3) → statine (49642-07-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 40 ℃; for 2.5h; under 760 Torr;

DOI:10.1246/cl.1999.687

upstream raw materials:

(3aR,5S,6aR)-5-((S)-1-Azido-3-methyl-butyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid

(3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid

(4S,5S)-5-isobutyl-4-hydroxy-2-oxopyrrolidine

Downstream raw materials:

(3S,4S)-4-(carbamic acid benzyl ester)-3-hydroxy-6-methyl-heptanoic acid

(4S,5S)-3-Benzyloxycarbonyl-5-ethenyl-4-isobutyl-2,2-dimethyloxazolidine

(4S,5S)-3-Benzyloxycarbonyl-5-formyl-4-isobutyl-2,2-dimethyloxazolidine

Methyl (4S,5S)-3-Benzyloxycarbonyl-5-(2-hydroxyethyl)-4-isobutyl-2,2-dimethyloxazolidine

Refernces

Inhibition of Aspartic Proteinases by Peptides Containing Lysine and Ornithine Side-Chain Analogues of Statine

10.1021/jm00385a010

The research focuses on the inhibition of aspartic proteinases by peptides containing lysine and ornithine side-chain analogues of statine. The purpose of this study was to design and synthesize new analogues of statine, specifically 4,8-diamino-3-hydroxyoctanoic acid ([LySta]) and 4,7-diamino-3-hydroxyheptanoic acid ([OrnSta]), based on substrate specificity and molecular modeling of three-dimensional structures. The goal was to develop selective and potent inhibitors for penicillopepsin, an aspartic proteinase. The researchers synthesized these new amino acids and used them to prepare inhibitors, measuring inhibition constants (Ki values) for their effects on porcine pepsin and penicillopepsin. The study concluded that the new inhibitors were significantly more potent against penicillopepsin than the original statine-containing inhibitor, with Ki values 10-100 times smaller, while being exceptionally weak inhibitors of porcine pepsin. The chemicals used in this process included Boc-Lys(Z)-a1, Boc-Orn(Bz1,Z)-a1, lithio ethyl acetate, trichloroethoxycarbonyl derivatives, and various other reagents and solvents for peptide synthesis and purification.

Renin inhibitors. Statine-containing tetrapeptides with varied hydrophobic carboxy termini

10.1021/jm00393a029

The research investigates a series of statine-containing tetrapeptides with modified carboxy termini to identify suitable replacements for the Phe residue in renin inhibitors. The study explores various hydrophobic aromatic groups to define optimal binding aspects in a region of the enzyme specific for spatial arrangement of aromatic groups. The chemicals involved include statine, a unique amino acid, and various aromatic amines such as benzylamine, phenethylamine, and derivatives like 1,2-diphenylethylamine, which are used to create the modified tetrapeptides. The research aims to achieve inhibitory potency in the nanomolar range against porcine kidney renin while also addressing discrepancies observed between human plasma and purified human kidney renin assays.

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