82267-36-5

Upstream product

• 2304-94-1 3-(benzyloxycarbonylamino)propanoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 
• 82267-34-3 4-benzyloxycarbonylamino-1-bromo-2-butanone 
• 865487-27-0 benzyl (2R,3R,4'S)-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate 
• 865487-55-4 benzyl (2R,3R)-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate 
• 116181-65-8 (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 
• 886-64-6 N^β-benzyloxycarbonyl-β-alaninamide 
• 82267-35-4 Diazo-(N-benzyloxycarbonyl-β-alanyl)methane 

Relevant academic research and scientific papers

SUSTAINED RELEASE DELIVERY SYSTEMS COMPRISING TRACELESS LINKERS

Described herein are drug delivery systems for delivering biologically active agents comprising primary or secondary amines, or a ring nitrogen atom of an azaheteroaryl ring, pharmaceutically acceptable salts thereof, drug delivery reagents related theret

Direct synthesis of phosphinopeptides containing C-terminal α-aminoalkylphosphinic acids

A series of phosphinopeptides containing C-terminal α- aminoalkylphosphinic acids were prepared in good yields directly in one-pot reactions of 2-(N-benzoxycarbonylamino)alkanamides/peptide amides, aldehydes, and aryldichlorophosphines, followed by hydrolysis. In the current method, the peptide bond was formed in a Mannichtype reaction. Springer-Verlag 2010.

EPC-synthesis of β-amino acid derivatives through lithiated hydropyrimidines

Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).

β-Secondary Kinetic Isotope Effects in the Clavaminate Synthase-Catalyzed Oxidative Cyclization of Proclavaminic Acid and in Related Azetidinone Model Reactions

Clavaminate synthase is an Fe(II)/α-ketoglutarate-dependent oxygenase that catalyzes three mechanistically distinct reactions in the course of clavulanic acid biosynthesis. Clavulanic acid is of significant chemical importance as a potent inhibitor/inactivator of β-lactamase enzymes, a prominent means of bacterial resistance to, for example, penicillin. Primary and α-secondary T(V/K) kinetic isotope effects have been determined in earlier work for the clavaminate synthase-catalyzed oxidative cyclization of proclavaminic acid, one of the three reactions mediated by this enzyme. In this paper the β-secondary deuterium kinetic isotope effect for this reaction has been determined using remote 3H and 14C labels in an attempt to distinguish between radical or cationic intermediates in the reaction as suggested by the magnitudes of the primary and secondary α-effects. The presence of the adjacent azetidinone nitrogen and the intervention of an azetinone intermediate, formally antiaromatic in the resonance form of the amide, make interpretation of the low β-secondary effect (1.056 ± 0.002 for dideuteriation at C-3′) problematic. To assist interpretation of this result, a 4-chloroazetidinone model system has been constructed dideuteriated at C-3 identically to proclavaminic acid and bearing remote radiolabels. Reaction of this substrate at 25°C under both radical and solvolysis conditions afforded β-secondary kinetic isotope effect data for direct comparison to the enzymic reaction. The measured effects are similarly small but strongly dependent on the polarity/acidity of the reaction medium. These results are discussed in terms of the commitment to catalysis and the extent to which amide resonance may be favored in the transition state of the oxidative cyclization.

Synthesis and Stereochemistry of Hypusine, a New Amino Acid in Bovine Brain

Hypusine, a new basic amino acid occurring in the homogenate of bovine brain tissue, was synthesized to determine the absolute structure.Nα-Benzyloxycarbonyl-L-lysine benzyl ester was coupled with (S)- or (R)-4-benzyloxycarbonylamino-1-bromo-2-butanol derived from L- or D-malic acid, respectively.The products were deprotected by catalytic dehydrogenation.One of the synthetic compounds, i.e., (2S,9R)-2,11-diamino-9-hydroxy-7-azaundecanoic acid, was completely identical with natural hypusine in all respects.