189101-41-5Relevant articles and documents
Enzymatic resolution of alicyclic β-lactams
Kaman, Judit,Forro, Eniko,Fueloep, Ferenc
, p. 1593 - 1600 (2000)
Racemates of N-hydroxymethylated β-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E>200) was observed when the enzymatic reactions were perfor
Application of a new chiral stationary phase containing the glycopeptide antibiotic A-40,926 in the direct chromatographic resolution of β-amino acids
D'Acquarica, Ilaria,Gasparrini, Francesco,Misiti, Domenico,Zappia, Giovanni,Cimarelli, Cristina,Palmieri, Gianni,Carotti, Angelo,Cellamare, Saverio,Villani, Claudio
, p. 2375 - 2385 (2000)
A new enantioselective HPLC procedure for the direct resolution of β-amino acids is described, based on the use of a new chiral stationary phase (CSP) containing the macrocyclic glycopeptide antibiotic A-40,926, structurally related to teicoplanin, covalently bonded to silica gel microparticles. The new CSP shows higher enantioselectivity and broader applicability in this field compared to the parent teicoplanin phase. The potential for semi-preparative separations on the A-40,926-CSP is demonstrated for a selected cyclic β-amino acid. Copyright (C) 2000 Elsevier Science Ltd.
PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION
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, (2010/04/25)
Peptides, peptidomimetics and derivatives thereof of the general formula I: H2N-GHRPX1-β-X4X5X6X7X8X9X10-X11 (I), in which X1-X10 denote one of the 20 genetically coded amino acids, wherein X8, X9 and X10 may also denote a single chemical bond;X11 denotes OR1 in which R1 equals hydrogen or (C1-C10) alkyl NR2R3 with R2 and R3 are equal or different and denote hydrogen, (C1-C10) alkyl, or a residue —W-PEG5-60K, in which the PEG residue is attached via a suitable spacer W to the N-atom, ora residue NH—Y-Z-PEG5-60K, in whichY denotes a chemical bond or a genetically coded amino acids from the group S, C, K or R andZ denotes a spacer, via which a polyethylene glycol (PEG)-residue can be attached, and their physiologically acceptable salts, andβ denotes an amino acid, or a peptidomimetic element, which induces a bend or turn in the peptide backbone.
A practical synthesis of enantiopure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine by asymmetric reductive amination and the Curtius rearrangement
Matsuo, Jun-ichi,Okano, Masahiko,Takeuchi, Kosuke,Tanaka, Hiroyuki,Ishibashi, Hiroyuki
, p. 1906 - 1910 (2008/02/13)
Enantiomerically pure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine was synthesized by the asymmetric reduction of a β-enamino ester formed from benzyl 2-oxocyclohexanecarboxylate and (R)-phenylethylamine, followed by hydrogenolysis, phthaloyla
Antiamyloid phenylsulfonamides: N-cycloalkylcarboxamides derivatives
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Page/Page column 7, (2010/02/11)
A series of N-cycloalkylcarboxamide derivatives of N-benzyl benzenesulfonamides of Formula I are described. The compounds inhibit β-amyloid peptide (β-AP) production and are useful in the treatment of Alzheimer's Disease and other conditions characterized
Synthesis of enantiopure cis- and trans-2-aminocyclohexane-1-carboxylic acids from octahydroquinazolin-4-ones
Priego, Jaime,Flores, Patricia,Ortiz-Nava, Claudia,Escalante, Jaime
, p. 3545 - 3549 (2007/10/03)
The chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[(S)-α-methylbenzyl]-4-quinazolinone 2 affords octahydroquinazolinones cis-3 and cis-4. Epimerization of cis-3 and cis-4 using t-BuO-K+ produces trans-5 and tra
Experimental determination of the absolute enantioselectivity of an antibody-catalyzed Diels-Alder reaction and theoretical explorations of the origins of stereoselectivity
Cannizzaro, Carina E.,Ashley, Jon A.,Janda,Houk
, p. 2489 - 2506 (2007/10/03)
The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene-1-carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition -state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.
An improved synthesis of enantiopure β-amino acids
Cimarelli,Palmieri,Volpini
, p. 2943 - 2953 (2007/10/03)
An improved method for the preparation of both the enantiopure β-amino acids is presented. The diastereomer benzyl β-amino esters, obtained by stereoselective reduction of β-enamino esters, were separated and hydrogenolyzed to the free enantiopure β-amino acids.
1, 2-Disubstituted cyclohexane derived tripeptide aldehydes as novel selective thrombin inhibitors
Harmat, Nicholas J.S.,Di Bugno, Cristina,Criscuoli,Giorgi, Raffaello,Lippi, Annalisa,Martinelli, Adriano,Monti, Susanna,Subissi
, p. 1249 - 1254 (2007/10/03)
A series of tripeptide arginine aldehydes was synthesized by replacement of proline with 1,2-disubstituted cyclohexane derivatives in the sequence of D-MePhe-Pro-Arg-H. Based on molecular modeling, further modification of the D-MePhe residue resulted in a potent and selective thrombin inhibitor.
