126399-04-0Relevant articles and documents
Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays
Clave,Ronco,Boutal,Kreich,Volland,Franck,Romieu,Renard
experimental part, p. 676 - 690 (2010/05/02)
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
Enantiospecific synthesis of N-Boc-Adda: a linear approach.
Pearson,Rinehart,Sugano,Costerison
, p. 2901 - 2903 (2007/10/03)
[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
Total synthesis of motuporin (nodularin-v)
Bauer, Shawn M.,Armstrong, Robert W.
, p. 6355 - 6366 (2007/10/03)
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
An asymmetric synthesis of ADDA, and ADDA-glycine dipeptide using the ss-lactam synthon method
Cundy, Darren J.,Donohue, Andrew C.,McCarthy, Tom D.
, p. 559 - 567 (2007/10/03)
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.
Towards an asymmetric synthesis of ADDA conjugates
Cundy, Darren J.,Donohue, Andrew C.,McCarthy, Tom D.
, p. 5125 - 5128 (2007/10/03)
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.
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
Beatty, Mark F.,Jennings-White, Clive,Avery, Mitchell A.
, p. 1637 - 1642 (2007/10/02)
(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
Total synthesis of N-phthaloyl adda methyl ester: All stereocenters originating from a single chiral epoxyalcohol
Chakraborty,Joshi
, p. 2043 - 2046 (2007/10/02)
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.
TOTAL SYNTHESIS OF ADDA, THE UNIQUE C20 AMINO ACID OF CYANOBACTERIAL HEPATOTOXINS
Namikoshi, Michio,Rinehart, Kenneth L.,Dahlem, Andrew M.,Beasley, Val R.,Carmichael, Wayne W.
, p. 4349 - 4352 (2007/10/02)
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).