13504-86-4

Usage

Uses

Used in Pharmaceutical Applications:
Z-CIS-HYP-OH is used as a therapeutic agent for promoting the production of collagen and other important proteins. It is particularly beneficial in treating conditions associated with collagen production, such as liver diseases and scleroderma.
Used in Scientific Research:
Z-CIS-HYP-OH is used as a research compound for studying its biosynthesis, metabolism, and function. Its health and economic impacts have sparked extensive research into understanding its role in protein synthesis and wound healing.
Used in Collagen Production:
Z-CIS-HYP-OH is used as a key component in the synthesis of collagen, which is essential for maintaining the structure and strength of tissues. This makes it an important factor in the development of treatments for conditions that affect collagen production and tissue integrity.

InChI:InChI=1/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 618-27-9 hydroxy L-proline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 67-56-1 methanol 
• 7732-18-5 water 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 942308-58-9 (2S,4S)-N-Cbz-4-hydroxyprolinol 
• 441067-49-8 (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 117811-78-6 methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate 
• 153093-07-3 C₁₃H₁₅NO₄ 
• 1365659-16-0 (1S,4S)-N-Cbz-6-(R/S)-hydroxy-5-oxa-2-aza-bicyclo[2.2.1]heptane 
• 1365659-15-9 (1S,4S)-N-Cbz-6-(R/S)-methoxy-5-oxa-2-aza-bicyclo[2.2.1]heptane 

Downstream Products

• 128019-80-7 (4S)-1-benzyloxycarbonyl-N-t-butyl-4-hydroxy-L-prolinamide 
• 57653-35-7 (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl 
• 165177-74-2 (4S)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-L-proline 
• 942308-58-9 (2S,4S)-N-Cbz-4-hydroxyprolinol 
• 77937-75-8 (2S,4S)-2-(anilinomethyl)-1-ethyl-4-hydroxy-pyrrolidine 
• 77937-78-1 (2S,4S)-2-phenylcarbamoyl-4-pyrrolidinyl acetate 
• 77937-79-2 (2S,4S)-1-acetyl-2-phenylcarbamoyl-4-pyrrolidinyl acetate 
• 84863-52-5 (2S,4S)-2-cyclohexylcarbamoyl-4-pyrrolidinyl acetate 
• 84846-31-1 (2S,4S)-2-(2,6-xylylcarbamoyl)-4-pyrrolidinyl acetate 
• 84846-35-5 (2S,4S)-1-acetyl-2-cyclohexylcarbamoyl-4-pyrrolidinyl acetate 
• 84846-38-8 (2S,4S)-1-acetyl-2-methylphenylcarbamoyl-4-pyrrolidinyl acetate 
• 84846-39-9 (2S,4S)-2-phenylcarbamoyl-1-pivaloyl-4-pyrrolidinyl acetate 
• 84846-36-6 (2S,4S)-1-acetyl-2-(2,6-xylylcarbamoyl)-4-pyrrolidinyl acetate 
• 84846-29-7 (2S,4S)-1-benzyloxycarbonyl-2-(methylphenylcarbamoyl)-4-pyrrolidinyl acetate 

Relevant academic research and scientific papers

Novel μ opioid antagonists derived from the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2)

Hybrid analogues of the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2, Dmt?=?2′,6′-dimethyltyrosine) containing cis-4-amino-Pro, trans-4-amino-Pro, cis-4-aminoethyl-Pro or cis-4-guanidinylethyl-Pro in the 2 p

DIMERIC PEPTIDE INHIBITORS OF APOPTOSIS PROTEINS

The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by lAPs. In particular the present compounds and compositions may be used to treat lAP-mediated ovarian cancer and hepatitis B infection.

Production of cis-4-hydroxyproline

PROBLEM TO BE SOLVED: To produce cis-4-hydroxyproline useful as a raw material of medicines and agrochemicals by an industrially suitable method.SOLUTION: The method for producing cis-4-hydroxyproline includes: hydrolyzing a hydroxyproline derivative represented by formula (1), wherein Rdenotes a 1-6C alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an aralkyloxycarbonyl group, in the presence of a hydrochloric acid catalyst; neutralizing the resultant with an organic base; and thereafter diluting the resultant with an alcohol.

Synthesis of (2S,4S)-4-hydroxyproline from D-glucose

Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.

SYNTHESIS OF PYRROLIDINE COMPOUNDS

Provided are methods for the preparation of certain substituted pyrrolidine compounds, forms of (2S, 4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride, and methods for preparing and using these forms.

METHOD FOR PREPARING (CIS)-4-HYDROXYPROLINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for preparing a (cis)-4-hydroxyproline derivative by a simple operation. SOLUTION: The (cis)-4-hydroxyproline derivative useful as an intermediate for drugs can be prepared in a good yield by a simple operation by adding a basic compound on the hydrolysis of a (trans)-4-hydroxyproline ester derivative to perform the reaction at a high temperature (50-120°C), and thereafter lowering the temperature of the reaction solution to 0-40°C to add the basic compound again.

Regioselective synthesis of nitrones by decarboxylative oxidation of N- alkyl-α-amino acids and application to the synthesis of 1-azabicyclic alkaloids

Tungstate-catalyzed oxidation of N-alkyl-2a-amino acids with 30% H2O2 solution under phase-transfer conditions gives nitrones regioselectively in good yields: Using this method, stereodivergent synthesis of (R)- and (S)-4- (t-butyldimethylsilyloxy)-1-pyrroline N-oxides ((R)-17a and (S)-17a) was achieved. In addition, (R)- and (S)-3-(t-butyldimethylsilyloxy)-1-pyrroline N-oxides ((R)-45 and (S)-45) were prepared by catalytic oxidation of the corresponding chiral pyrrolidines in a regioselective manner. These chiral cyclic nitrones, 17 and 45 are versatile intermediates for the synthesis of optically active nitrogen heterocycles, since stereoselective additions of carbon nucleophiles to these chiral nitrones can be readily performed. Typically, ZnI2-mediated addition of ketene t-butyldimethylsilyi methyl acetal (29a): to (R)-17a gave the' cis-adduct, methyl (2R,4R)-[1,4-bis(t- butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (cis-30). In contrast, the addition of lithium acetylides 34 to the nitrone (R)-17a gave the trans- adducts, (2S,4R)-2-(1-alkynyl)-4-(t-butyldimethylsilyloxy)-1- hydroxypyrrolidines trans-35. These adducts are useful intermediates for syntheses of the nitrogen heterocycles (3R,5R)-1-aza-3- hydroxybicyclo[3.3.0]octane (37) and (6R,8R)-1-aza-8- hydroxybicyclo[4.30]nonane (38), respectively. The ZnI2-mediated addition of ketene silyl acetal 29a to the nitrone (R)-45 gave methyl (2S, 3R)-[1,3- bis(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (trans-50a), which was used for asymmetric synthesis of the Geissman-Waiss lactone ((-)-49).

Sialyl Lewis X mimetics incorporating fucopeptides

Sialyl Lewis X mimetics incorporating fucopeptides are synthesized and shown to mimic the configuration and essential functional groups of sialyl Lewis X in space. The fucopeptides exhibit substantially the same biological activity as sialyl Lewis X in th

Method of inhibiting the transport of L-glutamate to treat CNS disorders

A method of inhibiting the transport of a neurotransmitter away from the synapse comprising contacting a neurotransmitter transporter with a compound having the structure STR1 wherein STR2 or CONHR 3 in any combination and and wherein R 2 =OR 3, NR 3 2, alkyl, or substituted alkyl and R 3 =alkyl or substituted alkyl.

Nucleosides and Oligonucleotides Derived from trans-4-Hydroxy-N-acetylprolinol

The 4-O-phosphoramidites of monomethoxytritylated 4-hydroxy-N-6-benzoyladenin-9-yl)acetyl>prolinol and 4-hydroxy-N-prolinol were prepared for incorporation into nucleic acids.The L-trans all-adenine oligonucleotide (ON) hybridises to natural oligothymidylate, apparently via triplex formation.All-purine sequences of the L-trans form can also form homo-complexes with their pyrimidine counterpart.The D-trans compounds give larger destabilisation when inserted in DNA.D-trans all-adenine ONs do not form complexes with natural oligothymidylate.For this series of modified ONs no hybridisation could be detected between complementary strands of opposite enantiomeric form.