Determination of the complete absolute configuration of petriellin A

Luigi Aurelio; Robert T.C. Brownlee; Jason Dang; Andrew B. Hughes; Gideon M. Polya

doi:10.1071/CH06148

Determination of the complete absolute configuration of petriellin A

Luigi Aurelio, Robert T.C. Brownlee, Jason Dang, Andrew B. Hughes, Gideon M. Polya

Medicinal Chemistry

Research output: Contribution to journal › Article › Research › peer-review

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Abstract

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.

Original language	English
Pages (from-to)	407-414
Number of pages	8
Journal	Australian Journal of Chemistry
Volume	59
Issue number	6
DOIs	https://doi.org/10.1071/CH06148
Publication status	Published - 14 Jul 2006

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abstract = "We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.",

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AU - Hughes, Andrew B.

AU - Polya, Gideon M.

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N2 - We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.

AB - We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.

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Determination of the complete absolute configuration of petriellin A

Abstract

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