121148-00-3

Usage

Uses

Used in Organic Synthesis:
N-Boc-trans-4-amino-L-proline methyl ester serves as a crucial building block in organic synthesis, facilitating the creation of a wide array of complex organic molecules. Its protected structure enables chemists to perform selective reactions, leading to more precise and efficient synthetic pathways.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N-Boc-trans-4-amino-L-proline methyl ester is utilized for the synthesis of peptides and peptidomimetics. Its protective Boc group allows for the controlled formation of peptide bonds and the development of bioactive molecules with potential therapeutic applications.
Used in the Development of Peptide-based Drugs:
N-Boc-trans-4-amino-L-proline methyl ester is employed as a key component in the development of peptide-based drugs. Its ability to be selectively modified contributes to the design of drugs with enhanced stability, bioavailability, and target specificity, which is vital for the treatment of various diseases and conditions.
Used in the Synthesis of Complex Molecules for Medicinal Chemistry:
N-Boc-trans-4-amino-L-proline methyl ester is also used in the synthesis of complex molecules for medicinal chemistry applications. Its protected structure provides a versatile platform for the attachment of various functional groups, enabling the creation of molecules with unique pharmacological properties and potential use in drug discovery and development.

InChI:InChI=1/C11H20N2O4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6,12H2,1-4H3/t7-,8+/m1/s1

Upstream product

• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 121147-97-5 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 334999-29-0 (2S,4S)-1-tert-butyl 2-methyl 4-bromopyrrolidine-1,2-dicarboxylate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 84520-68-3 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 
• 146060-25-5 O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 121147-94-2 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 121148-20-7 1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-04-7 1-tert-butyl 2-methyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-05-8 4(R)-[(phenylsulfonyl)amino]-1,2(S)-pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl)-2-methyl ester 
• 121148-18-3 1-tert-butyl 2-methyl (2S,4R)-4-(((4-methylphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-19-4 1-tert-butyl 2-methyl (2S,4R)-4-(((4-methoxyphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 922164-28-1 C₁₇H₂₃N₃O₆ 
• 922164-34-9 C₁₈H₂₆BrN₃O₄ 
• 1217446-43-9 (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester hydrochloride 
• 1360827-84-4 C₃₄H₃₈ClF₃N₈O₇S 
• 1360828-61-0 (2R,4S)-1-(tert-butoxycarbonyl)-4-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)pyrrolidine-2-carboxylic acid 
• 1360827-86-6 C₃₈H₄₃ClF₃N₉O₈S 
• 1360828-60-9 1-tert-butyl 2-methyl (2R,4S)-4-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)pyrrolidine-1,2-dicarboxylate 
• 1417629-84-5 5-[(2S,4R)-N-9-fluorenylmethoxycarbonyl-2-methoxycarbonyl-4-(3’-carbamidopropanoyl)aminopyrrolidineallyl]-5’-O-(4,4’-dimethoxytrityl)-3’-O-acetyl-2’-deoxyuridine 
• 1558041-39-6 3-ethyl-N-((3R,5S)-5-(ethylcarbamoyl)-1-(4-methoxybenzoyl)pyrrolidin-3-yl)-1-methyl-1Hpyrazole-5-carboxamide 

Relevant academic research and scientific papers

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

Aromatic heterocyclic derivative and application of derivative in drug

The invention discloses an aromatic heterocyclic derivative and application of the derivative in medicines and particularly provides an aromatic heterocyclic compound or a stereoisomer, a geometric isomer, a tautomer, nitrogen oxide, hydrate, solvate, metabolite, a pharmaceutically acceptable salt or prodrug thereof and a drug composition containing the compound. The invention further discloses application of the compound or its drug composition in drug preparation, and the drug is used for the treatment of respiratory diseases, especially chronic obstructive pulmonary disease (COPD).

HETEROAROMATIC DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF

Disclosed are heteroaryl derivatives, pharmaceutical composition and uses in the manufacture of a medicine for treating respiratory diseases, especially for chronic obstructive pulmonary disease (COPD).

Aromatic heterocyclic derivatives and applications of aromatic heterocyclic derivatives in medicines

The present invention discloses aromatic heterocyclic derivatives and applications of the aromatic heterocyclic derivatives in medicines, and specifically provides a class of aromatic heterocyclic compounds or stereoisomers, geometric isomers, tautomers, racemic bodies, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the compounds. The present invention further discloses uses of the compounds or pharmaceutical compositions in drug preparation, wherein the drug is used for treatment of respiratory diseases, particularly chronic obstructive pulmonary disease (COPD).

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.

Exploration of labeling by near infrared dyes of the polyproline linker for bivalent-type CXCR4 ligands

We have previously used poly-l-proline linkers for the development of bivalent-type ligands for the chemokine receptor, CXCR4. The bivalent ligands with optimum linkers showed specific binding to CXCR4, suggesting the existence of CXCR4 possibly as a dime

Remarkable structure effects on chiroptical properties of polyisocyanides carrying proline pendants

Chiral polymers with simple chemical structures and high helical conformation stabilities are important for their applications as chiral supports and asymmetrical catalysts. We report herein the synthesis of a series of aliphatic polyisocyanides carrying proline pendants of different chiralities, and an investigation of the effects of the chemical structures of these pendants on the chiroptical properties of the polymers. The configuration of the chiral center at the 4-position of the proline pendants was changed from S to R to check its effect on the handedness of the helical conformation. To examine the effects of steric hindrance on the stabilities of the helical conformation for these aliphatic representatives, proline pendants with various substituents at both the carboxyl and amine terminals were designed. To further examine the steric effects of the proline pendants, aromatic counterparts were also prepared. In the latter case, the effects of hydrogen bonds between pendant units on the enhancement and stabilities of the helical conformation were investigated by switching from the ester to an amide linkage. The Cotton effects and signal intensities of both aliphatic and aromatic polyisocyanides from circular dichroism spectroscopy were compared based on the bulkiness of the pendant groups, solvent polarities, and solution temperatures. It was found that highly stable helical conformations of polyisocyanides could be imposed by small bulky monoproline pendants. Twisted sisters: Polyisocyanides with various proline-based pendant groups were synthesized and their chiroptical properties investigated. These chiral polymers show unprecedented stable helical conformations in different solvents at various temperatures, even in the absence of strong hydrogen-bonding interactions between the pendant groups (see picture). Copyright

Synthesis of chiral pyrrolidine isostere inserted into pyrrole polyamide skeleton

An efficient and general route towards the synthesis of a series of chiral pyrrolidine pyrrole polyamide distamycin analogues starting from (L)-hydroxyproline is described. The binding abilities of these chiral pyrrolidine containing molecules to calf thymus DNA were evaluated by duplex DNA melting temperature analysis. The results revealed that both the chirality at the pyrrolidine ring and the site of incorporation plays an important role for binding at the duplex DNA.

Synthesis of deoxynucleoside triphosphates that include proline, urea, or sulfonamide groups and their polymerase incorporation into DNA

To expand the chemical array available for DNA sequences in the context of in vitro selection, I present herein the synthesis of five nucleoside triphosphate analogues containing side chains capable of organocatalysis. The synthesis involved the coupling

Synthesis of deoxynucleoside triphosphates that include proline, urea, or sulfonamide groups and their polymerase incorporation into DNA

To expand the chemical array available for DNA sequences in the context of in vitro selection, I present herein the synthesis of five nucleoside triphosphate analogues containing side chains capable of organocatalysis. The synthesis involved the coupling