The optimal conditions for the regioselective deprotection of per-N-Cbz-kanamycin A and the reaction mechanism was investigated. We found that the Cbz group at N-3″ position was selectively deprotected under milder basic conditions and the cyclic carbamate is an intermediate of the deprotection...

Aldol addition of dihydroxyacetone to N-Cbz-3-aminopropanal catalyzed by two d-fructose-6-phosphate aldolase variants, FSA A129S and FSA A129S/A165G, overexpressed in Escherichia coli was studied in microreactors. The presence of organic solvent was necessary due to poor solubility of N-Cbz-3-am...

This data article is related to the subject of a publication in Process Biochemistry, entitled “Chloroperoxidase-catalyzed amino alcohol oxidation: Substrate specificity and novel strategy for the synthesis of N-Cbz-3-aminopropanal” (Masdeu et al., 2016) [1]. Here, the products of the chemical...

The relative reactivities of the hydroxyl groups of methyl α- and β-D-xylopyranosides in selective sulfonylation reactions with methanesulfonyl chloride in pyridine have been determined. For the α-anomer, the order of reactivity is O-2> O-4>O-3, and for the β-anomer O-4>O-3>O-2. Useful yield...

Publisher SummaryThis chapter discusses sulfonic esters of carbohydrates. Of the various ways in which sulfonic esters may be synthesized, only two––the use of metallic salts of sulfonic acids and the use of suljonyl halides–– have so far achieved importance in carbohydrate chemistry. Certai...

Publisher SummaryThis chapter discusses the sulfonic esters of carbohydrates. Adequate methods for sulfonylation existed, and an introduced sulfonyl group provided a protecting group stable under acidic, neutral, and slightly basic conditions. Removal of the sulfonyl protecting group is known to...

The selectins play a key role in the inflammatory process, that is, the recruitment of leukocytes from blood vessels into inflamed tissue. Because excessive infiltration of leukocytes can induce acute or chronic reactions, the control of leukocyte extravasation is of great pharmaceutical interes...

The enantioselective synthesis of benzo-annulated oxa-heterocycles 2,3-dihydrobenzofuran and 1-benzopyran derivatives is described using β-hydroxy-α-tosyloxy esters as chiral building blocks, which are easily accessible through the regioselective α-tosylation of Sharpless asymmetric dihydroxy...

A general procedure is described for the regiospecific preparation of 1-substituted-5-hydroxy-1H-pyrazoles containing differentiated ester moieties at the 3- and 4-positions. This process involves the coupling of monosubstituted benzyl carbazates with various malonyl chlorides or acids, deprotec...

α-N-Acyloxyimino esters serve as highly efficient substrates for the N,N,C-trialkylation reaction that can introduce various patterns of nucleophiles at the imino nitrogen and carbon atoms to synthesize N,N-dialkylated and N,N,C-trialkylated α-amino esters in moderate to high yields.

A new bis-bidentate ligand, 1-[(5-methyl-2,2′-bipyridin-5′-yl)-methyl-1H-pyrazol-3-yl]-pyridine (L1), was designed and synthesized. The reactions of the ligand with [Cu(CH3CN)4]ClO4, Cu(ClO4)2·6H2O, AgNO3 and Cd(NO3)2·4H2O were carried out and dinuclear double helical complexes [CuI2L12][ClO...

Iminonickel(II) complexes have been prepared from the reaction of the iminoborate compounds with NiBr2 or Ni(acac)2 respectively, in the presence of 2,2′-bipyridine. The mechanism of formation and the crystal structure are discussed.

1,2-Di(2,2′-bipyridin-5-yl)ethane (BL1) and 1,2-di(2,2′-bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)2)(PF6)2 for the preparation of various [Ru(L)2(BL)Ru(L)2](PF6)4-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-...

Crystals of 9,9-(η2-2,2′-bipyridine)-2,7-bis(t-butyl)-dibenzoplatinol are monoclinic, space group P21/a; a 17.874, b 9.849, c 15.123 Å; α = γ = 90.00, β 109.51°; Z = 4; Dx 1.629, Dm 1.628 g cm−3, flotation method in CCl4/CHBr3; M = 615.7; Mo-Kα 0.71069 Å, graphite monochromator; F(000) = ...

A new bridging ligand, 1,3-bis(4′-methyl-2,2′-bipyridin-4-yl)propan-2-one (L) and its mono- and dinuclear Ru(II) complexes have been synthesized and characterized. The carbonyl group in L keeps its character and does not affect the Ru(II) moieties. In addition, the two Ru(II) terminuses of the...

The tumorigenic activities of four representative heterocyclic amine food pyrolysates, 2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1), 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ(, 2-amino-3,8-dimethylimidazo[4,5f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyr...

The mutagen and probable human carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) is metabolized in the colon to 9-hydroxyl-2,7-dimethyl-7,9,10,11-tetrahydropyrimido[2′,1′:2,3]imidazo[4,5-f]quinoxaline (MeIQx-M1) by conjugation with microbially generated acrolein. However, whethe...

The cytochrome P450 RauA from Rhodococcus erythropolis JCM 6824 catalyzes the hydroxylation of a nitrogen atom in the quinolone ring of aurachin, thereby conferring strong antibiotic activity on the aurachin alkaloid. Here, we report the crystal structure of RauA in complex with its substrate, a...

Aurachins, a family of isoprenoid quinoline alkaloids isolated from the myxobacterium Stigmatella aurantiaca, possess multiple interesting bioactivities and were subject of intensive studies of biosynthesis. In this Letter, we describe the efficient few step total synthesis of the parent compoun...

Peptide synthesis method was first employed to synthesize glidobamine, the core structure of the glidobactin antibiotics (2), but in a model study all attempts failed to cyclize the linear precursor 10. Then a NN bond cleavage method was developed to construct the ring skeleton of glidobamine (2...