- Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays
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A series of simplified microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for thei
- Clave,Ronco,Boutal,Kreich,Volland,Franck,Romieu,Renard
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experimental part
p. 676 - 690
(2010/05/02)
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- Enantiospecific synthesis of N-Boc-Adda: a linear approach.
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[structure: see text] Synthesis of the unusual amino acid (2S,3S,8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 1
- Pearson,Rinehart,Sugano,Costerison
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p. 2901 - 2903
(2007/10/03)
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- Total synthesis of motuporin (nodularin-v)
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The serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (mic
- Bauer, Shawn M.,Armstrong, Robert W.
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p. 6355 - 6366
(2007/10/03)
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- Total synthesis of motuporin and 5-[L-Ala]-motuporin
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Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N- methyldehydrobutyrine residue masked as a threonine, but significant C- terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-1 (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.
- Samy, Raghu,Kim, Hong Yong,Brady, Matthew,Toogood, Peter L.
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p. 2711 - 2728
(2007/10/03)
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- An asymmetric synthesis of ADDA, and ADDA-glycine dipeptide using the ss-lactam synthon method
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The paper describes the synthesis of the W-Boc lactam 4, and demonstrates that it is an important intermediate in the synthesis of dipeptide 5 (X = H, n = 0, R = Me), an analogue of the ADDA-GIu dipeptide 3. In addition we have described a mild method for the preparation of the amino acid salt ADDA-HC1, and provided synthetic methods, and full characterisation for the previously 'elusive' free amino acid ADDA.
- Cundy, Darren J.,Donohue, Andrew C.,McCarthy, Tom D.
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p. 559 - 567
(2007/10/03)
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- Towards an asymmetric synthesis of ADDA conjugates
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In order to develop a general synthesis of ADDA containing peptides, an asymmetric synthesis of the β-lactum 4 and initial investigations into its opening with aminoesters is described.
- Cundy, Darren J.,Donohue, Andrew C.,McCarthy, Tom D.
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p. 5125 - 5128
(2007/10/03)
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- A new stereoselective route to (2S, 3S, 8S, 9S, 4E, 6E)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda)
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N-Boc-Adda has been prepared in 15 steps and 9% overall yield from the readily available alcohol, 3-pentyne-2-ol, employing a route that includes two Claisen rearrangements.
- Kim, Hong Yong,Toogood, Peter L.
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p. 2349 - 2352
(2007/10/03)
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- Stereocontrolled Synthesis of (2S,3S,8S,9S,4E,6E)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic Acid (Adda), the Amino Acid Characteristic of Microcystins and Nodularin
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(4R,5S)-4-Methyl-5-phenyloxazolidin-2-one has been used as a chiral template to construct the 8S and 9S chiral centres of (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the 2S and 3S centres being derived from D-asp
- Beatty, Mark F.,Jennings-White, Clive,Avery, Mitchell A.
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p. 1637 - 1642
(2007/10/02)
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- Total synthesis of N-phthaloyl adda methyl ester: All stereocenters originating from a single chiral epoxyalcohol
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Selective ring opening of (2S,3R)-epoxide of 4-benzyloxy-cis-2-buten-1-ol either at 2- or 3-position ensures stereospecific construction of all the chiral centers of Adda.
- Chakraborty,Joshi
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p. 2043 - 2046
(2007/10/02)
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- TOTAL SYNTHESIS OF ADDA, THE UNIQUE C20 AMINO ACID OF CYANOBACTERIAL HEPATOTOXINS
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Synthetic (2S,3R)-3-Amino-4-hydroxy-2-methylbutanoic acid, γ-lactone, and (4S,5S)-2,4-dimethyl-5-methoxy-6-phenyl-2-hexen-1-ol were oxidized and linked to give (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda).
- Namikoshi, Michio,Rinehart, Kenneth L.,Dahlem, Andrew M.,Beasley, Val R.,Carmichael, Wayne W.
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p. 4349 - 4352
(2007/10/02)
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