112271-08-6

Usage

Uses

Used in Organic Synthesis:
(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester is used as a synthetic intermediate for the preparation of various organic compounds due to its reactive ester group and unique structural features.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester is used as a key building block in the development of new drugs, taking advantage of its specific enantiomeric configuration and steric properties to create chiral molecules with potential therapeutic applications.
Used in Materials Science:
(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester is utilized as a component in the synthesis of advanced materials, such as polymers and composites, where its aromatic and steric characteristics can contribute to the material's properties and performance.

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 37517-78-5 magnesium bis(3-ethoxy-3-oxopropanoate) 
• 35116-15-5 Dibasic magnesium salt of ethyl hydrogen malonate 
• 105-36-2 ethyl bromoacetate 
• 168774-14-9 (S)-1-(2'-t-butoxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole 
• 141-78-6 ethyl acetate 
• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 6148-64-7 ethyl potassium malonate 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 1247065-61-7 C₁₇H₂₁N₃O₃ 
• 18942-49-9 Boc-D-Phe-OH 
• 1071-46-1 hydrogen ethyl malonate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 1025722-65-9 ethyl (4S,2Z)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-3-[(trifluoromethanesulfonyl)oxy]pent-2-enoate 
• 1025723-03-8 ethyl (4S,2E)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-3-[(trifluoromethanesulfonyl)oxy]pent-2-enoate 
• 1345837-40-2 (S)-tert-butyl 1-(7-methoxy-2-oxo-2H-chromen-4-yl)-2-phenylethylcarbamate 
• 120742-17-8 ethyl (3S,4S)-3-hydroxy-4-amino-5-phenylpentanoate hydrochloride 
• 109667-69-8 (1'R,2'R)-N-<2,4-dihydroxy-4-oxo-1-(phenylmethyl)butyl>carbamic acid 1,1-dimethylethyl ester 
• 1271777-26-4 C₃₃H₄₈N₄O₇ 
• 1271777-32-2 C₂₃H₃₂N₄O₃ 
• 684643-49-0 H-(SS)-AHPPA-OEt 
• 116326-39-7 ES-6864 
• 119379-17-8 (3S,4S)-4-amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide 
• 119357-93-6 (3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide 

Relevant academic research and scientific papers

Solid-Phase Synthesis of β-Lactams via the Miller Hydroxamate Approach

(Matrix Presented) β-Lactams were prepared on solid phase starting from serine, threonine, or other β-hydroxyacids derived from naturally occurring amino acids and a resin bound hydroxylamine. The ring closure was carried out under Mitsunobu conditions. The amino group present on the β-lactam was used to assemble a short peptide. After a reductive cleavage with Sml2, β-lactam-containing peptides were obtained.

SYNTHESIS OF ASATINE AND ITS ANALOGUES BY HOMOGENEOUS ASYMMETRIC HYDROGENATION

Diastereoselective hydrogenation of N-protected γ-amino β-keto esters catalyzed by BINAP-Ru(II) complexes provides an efficient entry to the statine series with high enantiomeric purities.

Helices with additional H-bonds: crystallographic conformations of α,γ-hybrid peptides helices composed of β-hydroxy γ-amino acids (statines)

β-Hydroxy-γ-amino acids (Statines) are a class of naturally occurring non-ribosomal amino acids frequently found in many peptide natural products. Peptidomimetics constituted with statines have been used as inhibitors for various aspartic acid proteases. In contrast to the synthetic γ-amino acids, very little is known about the folding behavior of these naturally occurring β-hydroxy γ-amino acids. To understand the folding behavior of statines, three α,γ-hybrid peptides P1 (Ac-Aib-γPhe-Aib-(R, S)Phesta-Aib-γPhe-Aib-CONH2), P2 (Ac-Aib-γPhe-Aib-(S, S)Phesta-Aib-γPhe-Aib-CONH2), and P3 (Ac-Aib-γPhe-Aib-(S, S)Phesta-Aib-(S, S)Phesta-Aib-CONH2) were synthesized on solid phase and their helical conformations in single crystals were studied. Results suggest that both syn and anti diastereoisomers of statines can be accommodated into the helix without deviating overall helical conformation of α,γ-hybrid peptides. In comparison with syn diastereoisomer, the anti diastereoisomer was found to be directly involved in the intramolecular H-bonding with the backbone carbonyl groups (i to i + 3) similar to the backbone amide NHs in the helix.

Novel renin inhibitors containing derivatives of N-alkylleucyl-β-hydroxy-γ-amino acids

In search for new drugs lowering arterial blood pressure, which could be applied in anti-hypertensive therapy, research concerning agents blocking of renin-angiotensin-aldosteron system has been conducted. Despite many years of research conducted at many research centers around the world, aliskiren is the only one renin inhibitor, which is used up to now. Four novel potential renin inhibitors, having structure based on the peptide fragment 8-13 of human angiotensinogen, a natural substrate for renin, were designed and synthesized. All these inhibitors contain unnatural moieties that are derivatives of N-methylleucyl-β-hydroxy-γ-amino acids at the P2-P1' position: 4-[N-(N-methylleucyl)-amino]-3-hydroxy-7-(3-nitroguanidino)-heptanoic acid (AHGHA), 4-[N-(N-methylleucyl)-amino]-3-hydroxy-5-phenyl-pentanoic acid (AHPPA) or 4-[N-(N-methylleucyl)-amino]-8-benzyloxycarbonylamino-3-hydroxyoctanoic acid (AAHOA). The previously listed synthetic β-hydroxy-γ-amino acids constitute pseudodipeptidic units that correspond to the P1-P1' position of the inhibitor molecule. An unnatural amino acid, 4-methoxyphenylalanin (Phe(4-OMe)), was introduced at the P3 position of the obtained compounds. Three of these compounds contain isoamylamide of 6-aminohexanoic acid (ε-Ahx-Iaa) at the P2'-P3' position. The proposed modifications of the selected human angiotensinogen fragment are intended to increase bioactivity, bioavailability, and stability of the inhibitor molecule in body fluids and tissues. The inhibitor Boc-Phe(4-OMe)-MeLeu-AHGHA-OEt was obtained in the form of an ethyl ester. The hydrophobicity coefficient, expressed as log P varied between 3.95 and 8.17. In vitro renin inhibitory activity of all obtained compounds was contained within the range 10-6-10-9 M. The compound Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa proved to be the most active (IC50 = 1.05 × 10-9 M). The compounds Boc-Phe(4-OMe)-MeLeu-AHGHA-Ahx-Iaa and Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa are resistant to chymotrypsin.

Synthesis of tetrasubstituted symmetrical pyrazines from β-keto γ-amino esters: A mild strategy for self-dimerization of peptides

A facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-amino esters is reported. The scope of the reaction was examined by use of various amino acid side-chain functional groups andpeptides. The mil

Exploring β-hydroxy γ-amino acids (statines) in the design of hybrid peptide foldamers

The synthesis and characterization of syn and anti β-hydroxy γ-amino acid (statine) diastereoisomers, their utilization in the design of hybrid peptide foldamers, and their single crystal conformations are studied.

A facile transformation of amino acids to functionalized coumarins

The synthesis of novel chiral coumarins functionalized with proteinogenic amino acid side chains via N-protected γ-amino-β-keto esters and their incorporation into the cell permeable HIV-1 TAT peptide through the modified solid phase peptide synthesis are

NOVEL MULTIFUNCTIONAL PEPTIDASE INHIBITORS, ESPECIALLY FOR MEDICAL USE

The invention relates to compounds of the general formula (1) or the acid addition salts thereof with organic and/or inorganic acids; as well as to the use of the compounds of the general formula (1) in medicine.

Novel multifunctional peptidase inhibitors, especially for medical use

The invention relates to compounds of the general formula (1) or the acid addition salts thereof with organic and/or inorganic acids; as well as to the use of the compounds of the general formula (1) in medicine.

Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement

A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(ii) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.