104195-80-4Relevant articles and documents
Minutissamides E-L, antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.
Kang, Hahk-Soo,Sturdy, Megan,Krunic, Aleksej,Kim, Hyunjung,Shen, Qi,Swanson, Steven M.,Orjala, Jimmy
, p. 6134 - 6143 (2012)
The extract of UIC 10035, a strain obtained from a sample collected near the town of Homestead, South Florida, showed antiproliferative activity against MDA-MB-435 cells. Bioassay-guided fractionation led to the isolation of a series of cyclic lipodecapeptides, named minutissamides E-L (1-8). The planar structures were determined by analysis of HRESIMS, tandem MS, and 1D and 2D NMR data, and the stereoconfigurations were assigned by LC-MS analysis of the Marfey's derivatives after acid hydrolysis. Minutissamides E-L (1-8) exhibited antiproliferative activity against MDA-MB-435 cells with IC50 values ranging between 1 and 10 μM. The structures of minutissamides E-L (1-8) were closely related with those of the previously reported lipopeptides, puwainaphycins A-E and minutissamides A-D, characterized by the presence of a lipophilic β-amino acid and three non-standard amino acids NMeAsn, OMeThr and Dhb (α,β-dehydro-α-aminobutyric acid). The strain UIC 10035 was designated as cf. Anabaena sp. on the basis of morphological and 16S rRNA gene sequence analyses.
Syntheses of isotopically labelled L-?±-amino acids with an asymmetric centre at C-3
Harding, John R.,Hughes, Rachael A.,Kelly, Nicholas M.,Sutherland, Andrew,Willis, Christine L.
, p. 3406 - 3416 (2007/10/03)
Approaches are described to the synthesis of a series of isotopically labelled L-a-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13 and/or deuterium and labelling of the amine with nitrogen-15. ? The Royal Society of Chemistry 2000.
General Method for the Asymmetric Synthesis of anti-Diastereoisomers of β-Substituted L-2-Aminobutanoic Acids via Chiral Nickel(II) Schiff's Base Complexes of Dehydroaminobutanoic Acid. X-Ray Crystal and Molecular Structure of the Nickel(II) Complex of the Schiff's Base from <(Benzyl...
Belokon', Yuri N.,Sagyan, Ashot S.,Djamgaryan, Silva A.,Bakhmutov, Vladimir I.,Vitt, Sergei V.,et al.
, p. 2301 - 2310 (2007/10/02)
An efficient approach to the asymmmetric synthesis of (L)-allo-isomers of β-substituted α-aminobutanoic acid is described.The chiral NiII complex of a Schiff's base derived from (S)-o-benzophenone (BBP) and glycine was treated with acetaldehyde in MeOH.The addition proceeds with high diastereoselectivity to give, if catalysed by MeONa, the corresponding complex of (R)-threonine, and, if catalysed by Et3N, the corresponding complex of (S)-allo-threonine.The (R)-threonine complex was converted into the chiral NiII complex of dehydroaminobutanoic acid, and a X-ray diffraction structural study of its major isomer showed that the dehydroaminobutanoic acid moiety was in the E-configuration.The complex, in turn, entered into Michael addition reactions with nucleophiles, including MeOH, EtOH, PhSH, and PhCH2SH.The reaction proceeded with high diastereoselectivity, producing predominantly complexes of the allo-threonine derivatives (d.e. > 90percent).Diastereoisomerically and enantiomerically pure α-amino acids were obtained after chromatographic purification, decomposition of the complexes, and recovery of the initial chiral auxiliary, BBP.The thiol addition reaction is accompanied by a side reaction leading to the formation of sizeable amounts of the vinylglycine complex.An approach to the synthesis of optically active vinylglycine starting with racemic methionine is described.
