Ulicyclamide and ulithiacyclamide, two new small peptides from a marine tunicate

Ireland, Chris M.; Scheuer, Paul J.

doi:10.1021/ja00537a053

Cited by 156 publications

(104 citation statements)

References 3 publications

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“…with accurate mass measurements of these fragments (170), which were supported by NMR measurements. They also established the structures for patellamide A-C using the same strategy (171).…”

Section: Eckartsupporting

confidence: 52%

Mass spectrometry of cyclic peptides

Eckart

1994

Mass Spectrometry Reviews

103

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“…with accurate mass measurements of these fragments (170), which were supported by NMR measurements. They also established the structures for patellamide A-C using the same strategy (171).…”

Section: Eckartsupporting

confidence: 52%

Mass spectrometry of cyclic peptides

Eckart

1994

Mass Spectrometry Reviews

103

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“…Since 1980, when two of the first peptide secondary metabolites, ulicyclamide and ulithiacyclamide, were first discovered in marine organisms (Ireland and Scheuer, 1980), many RiPPs and/or NRPs have been discovered on an almost weekly basis. Some examples of these are shown in Figure 13.6.…”

Section: Ribosomal-and Nonribosomal-derived Peptides: a Virtually Unlmentioning

confidence: 99%

“…The structure of ulicyclamide and ulithiacyclamide was elucidated in 1980 by Ireland and Scheuer (Ireland and Scheuer, 1980), since when more than 70 azole/azoline-containing cyanobactins have been described from ascidians, sponges, or mollusks. These are structurally diverse, and range in size from six to eight amino acids with varying numbers and combinations of oxazoles, oxazolines, thiazoles, and thiazolines.…”

Section: 7mentioning

confidence: 99%

Marine Peptide Secondary Metabolites

Banaigs

Bonnard

Witczak

et al. 2014

Outstanding Marine Molecules

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A large pro port ion of the marine natural produc ts actu ally u n der clinical inve stigat ion are pept ide sec ondary metabolites with unusual amino acids re sidues. This growing f amily of compounds can be produced via tw o major p athw ays, r ibosomal and nonribosomal. In this c hapt er a re p re sent ed a nd illu strated, with a fe w f amou s examples, ribosomal-and n onribosomal-d erived pe ptides. Atte ntion is focused on fi ve families of biological ly a ctive marine p eptides of d iverse origin, ranging from the old est living ce ll of the world, the cyanobact eria, to more sophisticat ed organisms s uch a s tu nicates or mol lusk s. T he discu ssed pe ptides illu strate d iff erently th e s tructural fe atu re s and diversity f ound in mari ne-derived peptid es; laxaphycins as an example o f true pept ide s; dolast atins, didemnins and kahalalides are discuss ed in connectio n wit h their cl inical trials; a nd azole/azoli ne-c ontaining cyanobactins to exe m plif y the extra ord ina ry c hemi cal dive rs it y wit hin a single organism. Information abou t their biol ogical properties and mec hanisms of a ctio n is disc uss ed when available .

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“…has been demonstrated in the case of the Palauan organism by workers with the Japanese Marine Biotechnology Institute, who reported a "sunscreen effect" by mycosporine-like amino acids produced by the ascidian. 13 Chemistry/bioactivity: Palauan specimens of L. patella are the source of ulicyclamide 11 and ulithiacyclamide 12, 14 patellamides A-C 13-15, 15 preulithicyclamide 16, 16 and several other closely related cyclic peptides. 17, 18 Most of the cyclic peptides are cytotoxic to various degrees with ulithiacyclamide 12 being the most potent.…”

Section: Lissoclinum Patellamentioning

confidence: 99%