5458-06-0

Usage

InChI:InChI=1/C7H12N2O3/c10-4-2-1-3-5-6(11)9-7(12)8-5/h5,10H,1-4H2,(H2,8,9,11,12)

Upstream product

• 29070-06-2 5-(4-aminobutyl)-hydantoin 
• 5458-05-9 5-(4-hydroxy-butylidene)-imidazolidine-2,4-dione 
• 117043-44-4 5-tetrahydro[2]furyl-imidazolidine-2,4-dione 
• 79003-59-1 5-furan-2-yl-imidazolidine-2,4-dione 
• 74-90-8 hydrogen cyanide 
• 4221-03-8 5-hydroxypentanal 
• 151-50-8 potassium cyanide 
• 7732-18-5 water 
• 15719-64-9 methylammonium carbonate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 100720-20-5 N-[4-(2,5-dioxo-imidazolidin-4-yl)-butyl]-benzamide 
• 506-87-6 ammonium carbonate 
• 5107-18-6 N⁶-benzoyl-lysine 
• 7681-84-7 tetrahydrofuran-2-carbaldehyde 

Downstream Products

• 28484-49-3 DL-5-(δ-bromobutyl)hydantoin 
• 6033-32-5 (S)-2-amino-6-hydroxyhexanoic acid 
• 247578-23-0 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-hexanoic acid ((S)-1-hydroxymethyl-2-phenyl-ethyl)-amide 
• 24185-98-6 DL-indospicine 
• 142589-42-2 (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-hydroxy-(S)-norleucine methyl ester 
• 111581-88-5 [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester 
• 167090-40-6 (S)-2-amino-6-hydroxy-hexanoic acid methyl ester 
• 142589-43-3 (S)-2-[(S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-oxo-hexanoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 7,6-fused bicyclic lactams for use as beta-turn mimics

An improved synthesis of the 7,6-fused bicyclic lactam is presented starting from readily available chiral starting materials. (S)-allylglycine is protected as the phthalimide derivative and coupled with (S)-2-amino-6- hydroxyhexanoic acid methyl ester. Oxidation of the hydroxyl group to the aldehyde followed by enamide synthesis and acyl iminium ion cyclization provide the bicyclic system as a single diastereomer in good overall yield. Copyright Taylor & Francis Group, LLC.

Process development in the synthesis of the ACE intermediate MDL 28,726

MDL 28,726 is a key intermediate in the synthesis of the ACE inhibitors MDL 27,210A and MDL 100,240. An efficient nine-step synthesis of this tricyclic acid, which has three chiral centers, was developed beginning with 3,4-dihydro-2H-pyran. A key step in the synthesis features an enzyme-catalyzed resolution of the lithium salt of the W-trifluoroacetamide of (A,5)-6-hydroxynorleucine. All of the steps were optimized and completed in reactor equipment using environmentally acceptable processes. Process development of this route is described.

THE BIOCHEMICAL BASIS FOR THE DELETERIOUS EFFECTS OF L-CANAVANINE

L-Cavanine, L-2-amino-4-(guanidinooxy)butyric acid, is a potentially toxic analogue of L-arginine.Canavanine-sensitive organism activate and aminoacylate this non-protein amino acid and thereby create structurally aberrant, canavanine-containing proteins.Incorporation of canavanine into protein can alter the conformation and disrupt the function of the native macromolecule.Production of functionally impaired, canavanyl proteins affects developmental processes and contributes significantly to the expression of canavanine's potent antimetabolic properties in insects.Key Word Index: Canavalia ensiformis; Leguminosae; L-canavanine; non-protein amino acid; toxicity; canavanyl proteins; insects.