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N-Benzoyl-D-leucinol

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N-Benzoyl-D-leucinol
Category Others
Catalog number BBF-05203
CAS 1998687-23-2
Molecular Weight 221.29
Molecular Formula C13H19NO2
Purity >95% by HPLC

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Related CAS 257296-58-5 (L-configuration)
Synonyms Benzamide, N-[(1R)-1-(hydroxymethyl)-3-methylbutyl]-; N-[(2R)-1-Hydroxy-4-methyl-2-pentanyl]benzamide; (R)-N-(1-hydroxy-4-methylpentan-2-yl)benzamide
Storage Store at -20°C
IUPAC Name N-[(2R)-1-hydroxy-4-methylpentan-2-yl]benzamide
Canonical SMILES CC(C)C[C@H](CO)NC(=O)C1C=CC=CC=1
InChI InChI=1S/C13H19NO2/c1-10(2)8-12(9-15)14-13(16)11-6-4-3-5-7-11/h3-7,10,12,15H,8-9H2,1-2H3,(H,14,16)/t12-/m1/s1
InChI Key IFOWNENNSNMODK-GFCCVEGCSA-N
Boiling Point 415.1±28.0°C at 760 mmHg
Density 1.1±0.1 g/cm3
1. Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
Albrecht Berkessel, Santanu Mukherjee, Thomas N Müller, Felix Cleemann, Katrin Roland, Marc Brandenburg, Jörg-M Neudörfl, Johann Lex Org Biomol Chem. 2006 Dec 7;4(23):4319-30. doi: 10.1039/b607574f. Epub 2006 Nov 1.
This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Brønsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular, a "hit-structure" was identified which provides e.g.N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%.
2. Minimal structural requirements for agonist activity of PAR-2 activating peptides
Vincenzo Santagada, Giuseppe Caliendo, Beatrice Severino, Elisa Perissutti, Ferdinando Fiorino, Carla Cicala, Vincenzo De Filippis, Giuseppe Cirino Bioorg Med Chem Lett. 2002 Jan 7;12(1):21-4. doi: 10.1016/s0960-894x(01)00636-9.
Protease-activated receptor 2 (PAR-2) is involved in inflammatory, gastrointestinal, and vascular diseases. The aim of the present work was to elucidate the minimal structural features for PAR-2 agonist activity in short peptides. Our study resulted in the discovery of dipeptide derivatives of N(alpha)-benzoyl-Arg(NO(2))-Leu-NH(2) displaying a potency comparable to that of the full-length rat PAR-2 activating peptide (Ser-Leu-Ile-Gly-Arg-Leu-NH(2)).
3. Dynamic kinetic resolution of N-benzoyl-DL-amino acids via peptide bond forming reactions
T Miyazawa, T Hamada Protein Pept Lett. 2010 Apr;17(4):419-22. doi: 10.2174/092986610790963582.
Dynamic kinetic resolution (DKR) was demonstrated in the carbodiimide-mediated couplings of N-benzoyl-DL-amino acids with L-amino acid esters: the yields of the D-L-peptides significantly exceeded 50% in some cases. N-Benzoyl-DL-t-leucine afforded the D-L-peptide almost exclusively (up to 96% yield) in the reaction with methyl L-prolinate, which is the most efficient DKR obtained in the field of amino acids and derivatives.
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