Peptide Knowledge Center

Applications of unnatural amino acids

D-alanine can synthesize D-alanine alcohol and down to synthesize r-3-methylmorpholine, becoming an intermediate of Alzheimer's drugs


L-2-aminobutyric acid can synthesize l-2-aminobutylamide hydrochloride, which is the key intermediate for the synthesis of levetiracetam. Levetiracetam is a new antiepileptic drug developed by Belgium youshibi pharmaceutical company (UCB), which belongs to pyrrolidone cetam. It is one of the main drug series in the nervous system, and has the advantages of less adverse reactions, light and good tolerance; It is mainly used for the treatment of partial seizures in adults and children over 4 years old; In addition, it also has certain anti-inflammatory, analgesic and antidepressant effects.


L-n-valine is the main intermediate for the synthesis of perindopril. Perindopril is the third generation angiotensin converting enzyme inhibitor. It has the best antihypertensive effect 6 hours after taking, and the effect lasts for a long time. Perindopril can dilate large and small arteries, reduce blood volume, reduce systemic vascular resistance, left ventricular filling pressure and pulmonary capillary wedge pressure, increase cardiac output and stroke output, increase cardiac index without changing heart rate, improve exercise tolerance, reduce left ventricular myocardial hypertrophy, and improve hemodynamics. This product is well tolerated, will not cause hyperglycemia, and has no adverse effect on blood lipids. After taking perindopril, the inhibition of angiotensin converting enzyme (ACE) was slower than other inhibitors, but the inhibition rate of ace was more than 90%


D-valine is the intermediate of warnemulin hydrochloride. Valnemulin (VA) is a new generation of broad-spectrum truncated Pleurotus semisynthetic antibiotics, which belongs to diterpenes and is a special antibiotic for animals. D-phenylalanine is an intermediate for the synthesis of nateglinide. Nateglinide is a hard capsule with a white like content. It is a derivative of D-phenylalanine and belongs to non sulfonylurea hypoglycemic drugs. Its mechanism is mainly to block the opening of ATP sensitive potassium channels in islet cells by combining with sulfonylurea receptors on islet B cells, leading to depolarization of cell membrane, causing the opening of calcium channels and promoting insulin secretion. Nateglinide is a new type of postprandial blood glucose regulator, which can effectively control postprandial blood glucose level. It has the characteristics of fast onset, short action time, cardiovascular side effects and low incidence of hypoglycemia.


D-TRYPTOPHAN is the main intermediate in the synthesis of Tadanafil, which can treat male erectile dysfunction (ED). The principle of action is the same as that of sildenafil and vardenafil. Fmoc-Pen(Acm)-OH,Both rely on phosphodiesterase inhibitor (PDE-5) to improve the vasodilation of no by inhibiting the decomposition of cyclic guanosine phosphate (CGMP), so that ED patients can regain the ability of penis erection, N-Fmoc-7-methyl-L-tryptophan land Tadanafil is absorbed by intestines and stomach after taking it.


D-Tyrosine is a key intermediate of the anti heart failure drug sacubitril. Entresto is a combination of sacubitril, an enkephalinase inhibitor, and valsartan, an angiotensin II receptor blocker, to reduce the risk of cardiovascular death in patients with heart failure, hospitalization for chronic heart failure (nyhaii-iv) and decreased ejection fraction.


D-serine is the intermediate of laclamide, which is a drug for the treatment of epilepsy and neuropathic pain.


D-cysteine is an intermediate for the synthesis of Cefminox Sodium. Cefminox Sodium, also known as mexilin, Cefminox and meicilin, is a cephalosporin derivative, which is prepared by semi synthetic method. Its action property is similar to that of the third generation cephalosporins, and the finished product is heptahydrate. Its sodium salt is commonly used, which is white or yellowish white crystalline powder, soluble in water, and its action property is similar to that of the third generation cephalosporins.


D-Threonine is an intermediate for the synthesis of cefradine. Cefbuperazone (cefbuperazone) is a solid chemical, alias cefbuperazon, cefadroxime sodium, ethoxypiperone cephalosporin, capoazon, cephalosporin,Bupiprazole, cefobutazine, keiperazon, tomiporan, bmy-25182. The molecular formula is c22h29n9o9s2, the molecular weight is 627.651, and the melting point is 118~120 ℃. Clinically, it is used for septicemia, chronic bronchitis, pneumonia, pulmonary suppurative disease, endocarditis, cholecystitis, peritonitis, cystitis caused by Escherichia coli, Serratia, common and exotic Proteus, Haemophilus influenzae, pneumococcus and other sensitive bacteria.


L-tert leucine is the key side chain in the synthesis of antiviral drug azanavir. Azanavir, sold under the trade name reyataz, is an antiretroviral drug of protease inhibitor (PI). Like other antiretroviruses, it can be used to treat human immunodeficiency virus (HIV) infection.


The difference between azanavir and other Pi is that it can be given once a day (rather than multiple doses per day), and has a small impact on the patient's lipid distribution (the amount of cholesterol and other fatty substances in the blood). Like other protease inhibitors, azanavir is only used in combination with other HIV drugs.


The U.S. Food and Drug Administration (FDA) approved azanavir on June 20, 2003, which is the first PI approved for once daily administration, and has a low possibility of causing side effects such as lipodystrophy and cholesterol rise, so it can not be cross resistant with other PI. When ritonavir is used to strengthen, the metabolic advantage of azanavir will be reduced, but its efficacy is equivalent to that of lopinavir. It can be used for the remedial treatment of patients with a certain degree of drug resistance. It is one of the important drugs on the list of essential drugs of the World Health Organization and required by the basic health system.


D-proline is an intermediate for the synthesis of eletroptan, which can be used to treat migraine. The drug was originally developed by Pfizer company in the United States and was listed in 2001

The next chapter is about the synthetic methods of unnatural amino acids