157824-01-6Relevant articles and documents
Asymmetric Synthesis of the N-terminal component of Microginin: (2S,3R)-3-Amino-2-Hydroxydecanoic Acid, its (2R,3R)-Epimer and (3R)-Aminodecanoic Acid
Bunnage, Mark E.,Burke, Anthony J.,Davies, Stephen G.,Goodwin, Christopher J.
, p. 165 - 176 (1995)
3-Amino-2-hydroxydecanoic acid (AHDA) is a novel amino acid which has been suggested as the N-terminal component of the recently isolated angiotensin-converting enzyme inhibitor microginin.The naturally occurring amino acid was found to possess syn relati
Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide
Davies, Stephen G.,Epstein, Simon W.,Garner,Ichihara, Osamu,Smith, Andrew D.
, p. 1555 - 1565 (2007/10/03)
An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.
Asymmetric Synthesis of (2S,3R)-Amino-2-Hydroxydecanoic Acid: The Unknown Amino Acid Component of Microginin
Bunnage, Mark E.,Burke, Anthony J.,Davies, Stephen G.,Goodwin, Christopher J.
, p. 203 - 206 (2007/10/02)
3-Amino-2-hydroxydecanoic acid (AHDA) is an unusual amino acid purported to occur in the recently isolated angiotensin-converting enzyme inhibitor microginin.In order to elucidate the stereochemistry of the naturally occurring material, and thus complete
