Preparation of protected amino aldehydes

Stanfield, C. Freeman; Parker, James E.; KANELLIS, P.

doi:10.1021/jo00336a039

Cited by 59 publications

(25 citation statements)

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“…Although the aldehyde was produced, it was exceedingly labile in our hands. It has previously been reported that N-protected a-amino aldehydes are unstable (45), and the inability to generate aldehyde 4 and neopyochelin. The overall yield of synthetic pyochelin obtained in this study, approximately 5%, is certainly below the yield achieved in other siderophore syntheses (3).…”

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Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa

et al. 1988

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Pyochelin, a phenolic siderophore of Pseudomonas aeruginosa, was synthesized in three steps from salicylonitrile, L-cysteine, and L-N-methylcysteine. The synthetic product was determined to be identical to natural pyochelin by 1H nuclear magnetic resonance spectroscopy, fast atom bombardment mass spectrometry, chromatographic analysis, and chemical reactivity with FeCl3 and ammoniacal silver nitrate reagent. Synthetic and natural pyochelin promoted bacterial growth in iron-depleted medium and were also found to mediate iron transport by P. aeruginosa to the same levels. Neopyochelin, a stereoisomeric by-product of the synthesis, showed less biological activity than did pyochelin in iron transport assays.

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Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa

et al. 1988

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“…[15] A series of amino acid aldehydes (6) were synthesised from the corresponding amino acids using the method of Kanellis, [16] except after reduction of the protected amino acid with BH 3 -THF, the intermediate alcohols were oxidised using the Dess-Martin reagent. [17] Screening solvents (water, aqueous ethanol, ethanol) and bases (Na 2 CO 3 , K 2 CO 3 , triethylamine), we were pleased to see a good yield of the Pictet-Spengler product using triethyamine in alcohol at room temperature (rt).…”

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confidence: 99%

Diastereoselective Pictet–Spengler Reactions of a Tethered 2-Aminoimidazole

Shengule

Karuso

2014

Aust. J. Chem.

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The diastereoselective Pictet-Spengler reaction of aminopropyl-2-aminoimidazole with enantiopure aldehydes has been investigated. With amino acid-derived aldehydes, anti stereochemistry is favoured, with a diastereoselectivity up to 92 % achievable. The absolute stereochemistry of the products was determined through synthesis of a rigid derivative and from NMR data in combination with molecular modelling. The diastereoselectivity was shown to be dependent on the steric bulk of the amino acid side chain and independent of the nitrogen protecting group. Lewis acids catalysed the reaction but did not affect the diastereoselectivity.

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“…, prepared as described in literature, 12,13 was oxidized to aldehyde 5 [14][15][16] (Scheme 1) with NaOCl in the presence of a catalytic amount of 4-acetamido-2,2,6,6-tetramethylpiperidin-1-yloxy radical (AcNH-TEMPO). 17,18 N-Protected α-aminoaldehydes may be prepared either by reduction of a carboxy derivative of an amino acid or by oxidation of 2-aminoalcohols, and it is known that they have a high tendency for racemization.…”

Section: Resultsmentioning

confidence: 99%