81102-38-7

Usage

Uses

Used in Pharmaceutical Industry:
L-Proline, 4-hydroxy-, methyl ester, (4S)(9CI) is used as an intermediate in the synthesis of various pharmaceuticals, including anti-inflammatory drugs and antiviral agents, due to its unique structural properties that can be leveraged for medicinal chemistry.
Used in Peptide and Protein Production:
In the field of biochemistry, L-Proline, 4-hydroxy-, methyl ester, (4S)(9CI) serves as a building block for the production of specific peptides and proteins, contributing to the development of bioactive molecules with potential therapeutic applications.
Used in Biochemistry and Biotechnology Research:
L-Proline, 4-hydroxy-, methyl ester, (4S)(9CI) is utilized as a research tool in biochemistry and biotechnology, particularly for studying the properties and functions of amino acids and their derivatives, which is crucial for understanding fundamental biological processes and developing new biotechnological applications.
Used in Organic Synthesis:
L-Proline, 4-hydroxy-, methyl ester, (4S)(9CI) is employed as a reagent in organic synthesis, where it can be used to create a variety of complex organic molecules, highlighting its versatility in chemical reactions.

Upstream product

• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 67-56-1 methanol 
• 618-27-9 hydroxy L-proline 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 177186-28-6 (3S,6R,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione 
• 177186-30-0 (S)-2-((S)-1-Phenyl-ethylamino)-pent-4-enoic acid amide 
• 176966-58-8 (3S,5S)-5-Iodomethyl-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one 

Downstream Products

• 618-27-9 hydroxy L-proline 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 1216941-64-8 (2S,6S,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5, 6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydronaphthylcyclopropanoyl[e]pyrrolo[1,2-a][1,4] diazacyclopentadecyne-14a-carboxylate 
• 191280-88-3 (2S,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 1611480-82-0 (2S,4R)-methyl 4-azido-1-tritylpyrrolidine-2-carboxylate 
• 1363378-07-7 tert-butyl ((3R,5R)-5-fluoropiperidin-3 -yl)carbamate 
• 1611480-98-8 ((3R,5R)-3-amino-5-fluoropiperidin-1-yl)(phenyl)methanone 
• 1611481-35-6 ((2S,4R)-4-amino-1-tritylpyrrolidin-2-yl)methanol 
• 1611480-86-4 N-((3R,5S)-5-(hydroxymethyl)-1-tritylpyrrolidin-3-yl)benzamide 
• 1611487-82-1 N-((3R,5R)-5-fluoro-1-tritylpiperidin-3-yl)benzamide 
• 1611487-83-2 N-((3R,5R)-5-fluoropiperidin-3-yl)benzamide 

Relevant academic research and scientific papers

Glucosamine modified pentacyclic piperazine diketone and preparation and application thereof (by machine translation)

Aminoglucose-modified pentacyclic piperazinedione, and preparation and application thereofCH in the following formula is disclosed. 2 CO- Aminoglucose-modified pentacyclic piperazinedione The invention discloses a synthetic method thereof, disc

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Enantioselective synthesis and physicochemical properties of libraries of 3-amino- and 3-amidofluoropiperidines

The enantioselective syntheses of 3-amino-5-fluoropiperidines and 3-amino-5,5-difluoropiperidines were developed using the ring enlargement of prolinols to access libraries of 3-amino- and 3-amidofluoropiperidines. The study of the physicochemical properties revealed that fluorine atom(s) decrease(s) the pKa and modulate(s) the lipophilicity of 3-aminopiperidines. The relative stereochemistry of the fluorine atoms with the amino groups at C3 on the piperidine core has a small effect on the pK a due to conformationnal modifications induced by fluorine atom(s). In the protonated forms, the C-F bond is in an axial position due to a dipole-dipole interaction between the N-H+ and C-F bonds. Predictions of the physicochemical properties using common software appeared to be limited to determine correct values of pKa and/or differences of pK a between cis- and trans-3-amino-5-fluoropiperidines.

The implications of (2S,4S)-hydroxyproline 4-O-glycosylation for prolyl amide isomerization

The conformations of peptides and proteins are often influenced by glycans O-linked to serine (Ser) or threonine (Thr). (25,4R)-4-Hydroxyproline (Hyp), together with L-proline (Pro), are interesting targets for O-glycosylation because they have a unique influence on peptide and protein conformation. In previous work we found that glycosylation of Hyp does not affect the N-terminal amide transieis ratios (Ktrans/cis) or the rates of amide isomerization in model amides. The stereoisomer of Hyp-(25,4S)-4-hydroxyproline (hyp)-is rarely found in nature, and has a different influence both on the conformation of the pyrrolidine ring and on Ktrans/cis Glycans attached to hyp would be expected to be projected from the opposite face of the prolyl side chain relative to Hyp; the impact this would have on K trans/cis was unknown. Measurements of 3J coupling constants indicate that the glycan has little impact on the Cy-endo conformation produced by hyp. As a result, it was found that the D-galactose residue extending from a Cy-endo pucker affects both K trans/cis and the rate of isomerization, which is not found to occur when it is projected from a Cy-exo pucker; this reflects the different environments delineated by the proline side chain. The enthalpic contributions to the stabilization of the trans amide isomer may be due to disruption of intramolecular interactions present in hyp; the change in enthalpy is balanced by a decrease in entropy incurred upon glycosylation. Because the different stereoisomers-Hyp and hyp-project the O-linked carbohydrates in opposite spatial orientations, these glycosylated amino acids may be useful for understanding of how the projection of a glycan from the peptide or protein backbone exerts its influence.

BICYCLIC PYRAZOLE DERIVATIVE

A compound represented by the following formula (I), a prodrug thereof, or a pharmaceutically acceptable salt of either. These are compounds having high DPP-IV inhibitory activity and improved in safety, nontoxicity, etc. (I) [In the formula, R1 represents hydrogen, optionally substituted alkyl, etc.; the solid line and dotted line between A1 and A2 indicate a double bond (A1=A2), etc.; A1 represents a group represented by the formula C(R2), etc.; A2 represents a group represented by the formula C(R4), etc.; R2 represents hydrogen, optionally substituted alkyl, etc.; R4 represents hydrogen, optionally substituted alkyl, etc.; R6 represents hydrogen, optionally substituted aryl, etc.; and -Y represents, e.g.; a group represented by the formula (A): (A) (wherein ml is 0, 1, 2, or 3; and R7 is absent, or one or two R7's are present and each independently represents optionally substituted alkyl, etc.).]

Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.

Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively. The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization.