@article {2183,
	title = {Intraannular Savige-Fontana reaction: One-step conversion of one class of monocyclic peptides into another class of bicyclic peptides},
	journal = {Chemistry-a European Journal},
	volume = {14},
	number = {11},
	year = {2008},
	note = {ISI Document Delivery No.: 291XITimes Cited: 1Cited Reference Count: 34May, Jonathan P. Perrin, David M.},
	pages = {3404-3409},
	type = {Article},
	abstract = {Cyclisation and cross-linking strategies are important for the synthesis of cyclic and bicyclic peptides. These macrolactams are of great interest due to their increased biological activity compared to linear analogues. Herein, we describe the synthesis of a cyclic peptide containing an Hpi toxicophore, reminiscent of phakellistatins and omphalotins. The first intraannular cross-linking of such a peptide is then presented: using neat TFA to catalyse a Savige-Fontana tryptathionylation, the Hpi-containing peptide is converted to a bicyclic amatoxin analogue. As such, this methodology represents an efficient cyclisation method for cross-linking peptides and exposes a heretofore unrealised relationship between two different classes of peptide natural products. This finding increases the degree of potential chemical space for library generation.},
	keywords = {2-CHLOROTRITYL CHLORIDE, 2-THIOETHER DERIVATIVES, amatoxin, ANALOGS, CROSS-LINKING, CYSTEINE SULFHYDRYL-GROUPS, ILE3-AMANINAMIDE, indole, ISOPHAKELLISTATIN-3, natural products, OXIDATION, PEPTIDES, PHALLOTOXINS, RNA POLYMERASE-II, TRYPTOPHAN},
	isbn = {0947-6539},
	url = {<Go to ISI>://000255230200019},
	author = {May, J. P. and Perrin,David M.}
}
@article {1195,
	title = {High yielding synthesis of 3a-hydroxypyrrolo[2,3-b]indoline dipeptide methyl esters: Synthons for expedient introduction of the hydroxypyrroloindoline moiety into larger peptide-based natural products and for the creation of tryptathionine bridges},
	journal = {Journal of Organic Chemistry},
	volume = {70},
	number = {21},
	year = {2005},
	note = {ISI Document Delivery No.: 971SRTimes Cited: 12Cited Reference Count: 33},
	month = {Oct},
	pages = {8424-8430},
	type = {Article},
	abstract = {This work describes a rapid and high yielding oxidation of 14 tryptophanylated amino acid methyl esters to the corresponding 3 alpha-hydroxypyrrolo[2,3-b]indoline (Hpi) amino acids with generally facile separation of syn-cis and anti-cis diastereomers. Structural X-ray diffraction data are presented for both diastereomers of Tr-Hpi-Gly-OMe, which allow for a putative assignment of the other 13 pairs of diastereomers reported herein, based on correlations with H-1 NMR chemical shifts. Selective and high yielding deprotection at either the N or C terminus is described, allowing the Hpi motif to be introduced efficiently into potential targets with minimal protecting group manipulation. Two tripeptides containing Hpi and cysteine were prepared and treated with acid in the Savige-Fontana reaction to produce a cyclic tryptathionine linkage, characteristic of both amatoxins and phallotoxins.},
	keywords = {ANALOGS, ASYMMETRIC EPOXIDATION METHOD, CONFIGURATION, CONFORMATION, CYCLIZATION, CYSTEINE SULFHYDRYL-GROUPS, DERIVATIVES, HIMASTATIN, OXYGENATION, TRYPTOPHAN},
	isbn = {0022-3263},
	url = {<Go to ISI>://000232405500022},
	author = {May, J. P. and Fournier, P. and Pellicelli, J. and Patrick, B. O. and Perrin,David M.}
}
