81083-58-1Relevant articles and documents
Two separate and distinct syntheses of stereospecifically deuteriated samples of (2S)-proline
Barraclough, Paul,Dieterich, Petra,Spray, Caroline A.,Young, Douglas W.
, p. 1483 - 1491 (2006)
Two distinct syntheses of samples of the amino acid l-proline which are stereospecifically deuteriated on the β-carbon atom are reported. In the first of these, the labelled diazoketones 6, prepared by a chemico-enzymatic synthesis, have been photolysed in alkaline conditions to give the corresponding labelled methyl pyroglutamates 10 via hydrolysis and intramolecular trapping of the resultant ketene intermediates 9. These were then converted into (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H 2]-proline, 1a and 1b respectively. The second synthesis provides (2S)-[3,3-2H2]-, (2S,3S)- and (2S,3R)-[3- 2H1]-proline, 1d, 1a and 1c respectively, and has as its key step the highly stereoselective hydrolysis of the silylenol ethers 14 and 14a respectively in which deuteriation or protonation occurs from the re-face of the enol ether. The Royal Society of Chemistry 2006.
Calyxamides A and B, cytotoxic cyclic peptides from the marine sponge Discodermia calyx
Kimura, Miki,Wakimoto, Toshiyuki,Egami, Yoko,Tan, Karen Co,Ise, Yuji,Abe, Ikuro
experimental part, p. 290 - 294 (2012/05/05)
Cyclic peptides containing 5-hydroxytryptophan and thiazole moieties were isolated from the marine sponge Discodermia calyx collected near Shikine-jima Island, Japan. The structures of calyxamides A (1) and B (2), including the absolute configurations of all amino acids, were elucidated by spectroscopic analyses and degradation experiments. The structures are similar to keramamides F and G, previously isolated from Theonella sp. The analysis of the 16S rDNA sequences obtained from the metagenomic DNA of D. calyx revealed the presence of Candidatus Entotheonella sp., an unculturable δ-proteobacterium inhabiting the Theonella genus and implicated in the biosynthesis of bioactive peptides.