175671-49-5Relevant academic research and scientific papers
An Efficient Approach to the Family of 4-Substituted Pipecolic Acids. Syntheses of 4-Oxo-, cis-4-Hydroxy-, and trans-4-Hydroxy-L-pipecolic Acids from L-Aspartic Acid
Golubev, Alexander,Sewald, Norbert,Burger, Klaus
, p. 2037 - 2040 (1995)
Syntheses of 4-oxo-, cis-4-hydroxy-, and trans-4-hydroxy-L-pipecolic acids from L-aspartic acid using hexafluoroacetone as protecting reagent are described.Combination of a Stille cross-coupling reaction with subsequent Lewis acid catalyzed intramolecular Michael addition provides 4-oxo-L-pipecolic acid 5 or trans-6-methyl-4-oxo-L-pipecolic acid.Borohydride reduction of the protected 4-oxo-L-pipecolic acid derivative gives the corresponding cis-4-hydroxy-L-pipecolic acid 8.The trans isomer 10 is obtained in good yield via Mitsunobu inversion. - Key words: 4-Oxo-L-pipecolic acid, 4-hydroxy-L-pipecolic acids, L-aspartic acid, hexafluoroacetone, intramolecular Michael addition, Stille reaction
CIS-4-HYDROXYPIPECOLIC ACID AND 2,4-CIS-4,5-TRANS-4,5-DIHYDROXYPIPECOLIC ACID FROM CALLIANDRA
Romeo, John T.,Swain, Lee A.,Bleecker, Anthony B.
, p. 1615 - 1618 (1983)
Cis-4-hydroxypipecolic acid and 2,4-cis-4,5-trans-4,5-dihydroxypipecolic acid were isolated from leaves of Calliandra pittieri.A system for resolving the eight imino acids isolated from Calliandra is described.Key Word Index - Calliandra pittieri; Mimosoideae; cis-4-hydroxypipecolic acid; 2,4-cis-4,5-trans-4,5-dihydroxypipecolic acid; imino acid; pipecolic acid derivatives; stereoisomers.
Damipipecolin and damituricin, novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella damicornis
Aiello, Anna,Fattorusso, Ernesto,Giordano, Antonella,Menna, Marialuisa,Mueller, Werner E.G.,Perovic-Ottstadt, Sanja,Schroeder, Heinz C.
, p. 5877 - 5887 (2007)
Two new bromopyrrole alkaloids, damipipecolin (1) and damituricin (2), have been isolated from the Mediterranean sponge Axinella damicornis, and their structures established through spectroscopic methods. Compounds 1 and 2 extend the structural variety of
Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
Davis, Franklin A.,Chao, Bin,Andemichael, Yemane W.,Mohanty, Pradyumna K.,Fang, Tianan,Burns, David M.,Rao, Ashwin,Szewczyk, Joanna M.
, p. 486 - 492 (2002)
Enantiopure N-sulfinyl-δ-amino-β-ketoesters and isoquinolones, prepared from sulfinimines (N-sulfinyl imines) are a new class of polyfunctionalized chiral building blocks. These building blocks provide easy access to enantiomerically pure, functionalized piperidines and tetrahydroisoquinolines with a minimum of chemical manipulation and protecting-group chemistry.
CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Paragraph 00293-00294; 00299; 00693-00694; 00698; 00724, (2019/06/11)
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.
TUBULYSIN ANALOGUES AS ANTICANCER AGENTS AND PAYLOADS FOR ANTIBODY-DRUG CONJUGATES AND METHODS OF TREATMENT THEREWITH
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Page/Page column 146, (2019/06/17)
In one aspect, the present disclosure provides tubulysin analogs of the formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect
Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins with Highly Potent Cytotoxicities against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates
Nicolaou,Erande, Rohan D.,Yin, Jun,Vourloumis, Dionisios,Aujay, Monette,Sandoval, Joseph,Munneke, Stefan,Gavrilyuk, Julia
supporting information, p. 3690 - 3711 (2018/03/21)
Improved, streamlined total syntheses of natural tubulysins such as V (Tb45) and U (Tb46) and pretubulysin D (PTb-D43), and their application to the synthesis of designed tubulysin analogues (Tb44, PTb-D42, PTb-D47-PTb-D49, and Tb50-Tb120), are described.
2-Keto-3-Deoxy-l-Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives
Hernández, Karel,Gómez, Ariadna,Joglar, Jesús,Bujons, Jordi,Parella, Teodor,Clapés, Pere
, p. 2090 - 2100 (2017/06/23)
4-Hydroxy-2-keto acid derivatives are versatile building blocks for the synthesis of amino acids, hydroxy carboxylic acids and chiral aldehydes. Pyruvate aldolases are privileged catalysts for a straightforward access to this class of keto acid compounds. In this work, a Class II pyruvate aldolase from Escherichia coli K-12, 2-keto-3-deoxy-l-rhamnonate aldolase (YfaU), was evaluated for the synthesis of amino acid derivatives of proline, pipecolic acid, and pyrrolizidine-3-carboxylic acid. The aldol addition of pyruvate to N-protected amino aldehydes was the key enzymatic aldol addition step followed by catalytic intramolecular reductive amination. The corresponding N-Cbz-amino-4-hydroxy-2-keto acid (Cbz=benzyloxycarbonyl) precursors were obtained in 51–95% isolated yields and enantioselectivity ratios from 26:74 to 95:5, with chiral α-substituted N-Cbz-amino aldehydes. (S)-N-Cbz-amino aldehydes gave aldol adducts with preferentially (R)-configuration at the newly formed stereocenter, whereas the contrary is true for (R)-N-Cbz-amino aldehydes. Addition reactions to achiral amino aldehydes rendered racemic aldol adducts. Molecular models of the pre-reaction ternary complexes YfaU-pyruvate enolate-acceptor aldehyde were constructed to explain the observed stereochemical outcome of the reactions. Catalytic reductive amination of the aldol adducts yielded 4-hydroxy-2-pipecolic acid, and unprecedented C-5 substituted 4-hydroxyproline and pyrrolizidine-3-carboxylic acid derivatives. (Figure presented.).
Betaines and related ammonium compounds in chestnut (Castanea sativa Mill.)
Servillo, Luigi,Giovane, Alfonso,Casale, Rosario,Balestrieri, Maria Luisa,Cautela, Domenico,Paolucci, Marina,Siano, Francesco,Volpe, Maria Grazia,Castaldo, Domenico
, p. 1301 - 1309 (2015/11/09)
Chestnut fruits, being poor of simple sugars and consisting mainly of fibers and starch, are among the constituents of Mediterranean diet. While numerous studies report on content of proteins and amino acids in chestnut, no one has appeared so far on betaines, an important class of nitrogen compounds ubiquitous in plants for their protective action in response to abiotic stress. In this study, we analyzed by HPLC-ESI-tandem mass spectrometry, in fruits and flours of varieties of chestnut cultivated in Italy, the composition of betaines and ammonium compounds intermediates of their biosynthesis. Besides the parent amino acids, the compounds quantified were choline, glycerophosphocholine, phosphocholine, glycine betaine, N-methylproline, proline betaine (stachydrine), β-alanine betaine, 4-guanidinobutyric acid, trigonelline, N,N,N-trimethyllysine. Interestingly, some uncommon derivatives of pipecolic acid, such as N-methylpipecolic acid, 4-hydroxypipecolic acid and 4-hydroxy-N-methylpipecolic acid were identified for the first time in chestnut samples and characterized by MSn tandem mass spectrometry.
AN ENANTIOSELECTIVE PROCESS FOR THE SYNTHESIS OF (2S,4R)-4-HYDROXYPIPECOLIC ACID
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Page/Page column 24; 25, (2016/08/23)
The present invention relates to an improved process for synthesis of 4-hydroxy pipecolic acid. The present invention relates to an improved enantioselective process for the synthesis of (2S,4R)-4-hydroxypipecolic acid via Co(III) (salen)-catalyzed two stereocentered Hydrolytic Kinetic Resolution (HKR) of racemic 1,3-azido epoxide with good yields and high optical purity without any protecting groups. 10 31
