Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, N-acetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters.
N-acetyl-4-nitrotryptophan methyl ester (2), N-acetyl-5-nitrotryptophan methyl ester (3), N-acetyl-6-nitrotryptophan methyl ester (4) and N-acetyl-7-nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF(3)-methanol. Assignments of the (1)H and (13)C NMR chemical shifts were made using a combination of (1)H-(1)H COSY, (1)H-(13)C HETCOR and (1)H-(13)C selective INEPT experiments.
King
Russell R
RR
Potato Research Centre, Agriculture and Agric-Food Canada, PO Box 20280, Fredericton, NB, Canada, E3B 4Z7. kingr@agr.gc.ca
Calhoun
Larry A
LA
D000107:Acetylation; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014364:Tryptophan / Q000737:chemistry
D004952:Esters; D017672:Nitrogen Compounds; D014364:Tryptophan