Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays.
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 their binding affinity by the monoclonal antibody mAb MC159, an anti-microcystin-LR mAb recently selected by us for the detection of microcystins through various immunoassay formats. Some modifications have been brought to the enantiospecific synthesis of N-Boc-Adda developed by Pearson et al. (Org. Lett., 2000, 2, 2901) which enabled us to access in an economical and time-saving manner a small library of MC-LR linear analogues. Among which Adda was chosen to synthesise, as an illustrative example, a fluorescent probe derived from this beta-amino acid. This probe was subsequently solid-phase immobilised by means of oxime ligation in order to lead to biochips suitable for microcystin detection through the SPIT-FRI method.
Clavé
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Equipe de Chimie Bio-Organique, COBRA-CNRS UMR 6014 & FR 3038, rue Lucien Tesnière, 76131 Mont-Saint-Aignan, France.
Ronco
C
C
Boutal
H
H
Kreich
N
N
Volland
H
H
Franck
X
X
Romieu
A
A
Renard
P-Y
PY
D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000911:Antibodies, Monoclonal / Q000276:immunology; D003429:Cross Reactions; D003652:Decanoic Acids / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D005898:Glass / Q000737:chemistry; D055767:Immobilized Proteins / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D007118:Immunoassay / Q000379:methods*; D007202:Indicators and Reagents / Q000737:chemistry; D007700:Kinetics; D052998:Microcystins / Q000737:chemistry*; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry* / Q000276:immunology; D013237:Stereoisomerism
D000447:Aldehydes; D000577:Amides; D000911:Antibodies, Monoclonal; D003652:Decanoic Acids; D005456:Fluorescent Dyes; D055767:Immobilized Proteins; D007202:Indicators and Reagents; D052998:Microcystins; D010446:Peptide Fragments; C465008:phenyldecanoic acid; C078588:microcystin; C116609:3-hydroxybutanal