4779-31-1Relevant articles and documents
Manipulating L-aspartic and L-glutamic acids - Diastereoselective synthesis of enantiopure β-amino-γ-hydroxy acids and γ-amino-δ-hydroxy acids
Andres, Jose M.,Munoz, Eva M.,Pedrosa, Rafael,Perez-Encabo, Alfonso
, p. 3387 - 3397 (2007/10/03)
Enantiopure (3S,4R)- and (3S,4S)-3-amino-4-hydroxyhexanoic acids and (4S,5R)- and (4S,5S)-4-amino-5-hydroxyheptanoic acid derivatives have been prepared by stereodivergent synthesis from L-aspartic and L-glutamic acids, respectively. The stereochemistry at the carbon atom attached to the amino group was determined from the starting material but the configuration at C-4 or C-5 is controlled by diastereoselective alkylation with diethylzinc or ethylmagnesium bromide. The protection of the carboxylic group as OBO orthoester improved the yields in the final products. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2003.
Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids
Burtin, Guillaume,Corringer, Pierre-Jean,Young, Douglas W.
, p. 3451 - 3459 (2007/10/03)
Protected (4S)-4-carboxytetrahydro-1,3-oxazin-6-ones have been synthesised either by Baeyer-Villiger reaction on a 4-ketoproline derivative or, more directly, from an aspartate derivative. Two strategies have been used to develop these compounds as chiral templates in the synthesis of β-substituted aspartic acids. In the first, formation of an enaminone using Bredereck's reagent, followed by reaction with a Grignard reagent gave a series of alkylidene derivatives which could be reduced from the less hindered side by heterogeneous catalytic hydrogenation to give cis-oxazinones in a completety stereoselective manner. Alternatively, an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones were converted to β-substituted aspartic acids and to regioselectively protected β-substituted aspartic acids without loss of stereochemistry ar either centre.
Synthesis of suitably protected hydroxymethylene phosphonate- and 'phosphate phosphonate'-analogues of phosphoserine and their incorporation into synthetic peptides
Wiemann, Arndt,Frank, Ronald,Tegge, Werner
, p. 1331 - 1337 (2007/10/03)
Two suitably protected derivatives of phosphoserine 1 have been prepared in which the regular ester-oxygen is replaced by either a hydroxymethylene moiety or by a phosphorylated hydroxymethylene moiety. The second derivative termed 'phosphate phosphonate'
Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones
Burtin, Guillaume,Corringer, Pierre-Jean,Hitchcock, Peter B.,Young, Douglas W.
, p. 4275 - 4278 (2007/10/03)
Oxazinones have been synthesised and used as chiral templates in the synthesis of β-substituted aspartic acids. Use of a Bredereck's reagent/Grignard/hydrogenation strategy gave cis-oxazinones with complete stereoselectivity, whereas an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones could be converted to β-substituted aspartic acids and to regioselectively protected β-substituted aspartic acids without loss of stereochemistry at either centre.
Synthesis of Selectively Multi-Labelled Histidines with Stable Isotopes and Chiral Synthesis of L-Histidine from L-Aspartic Acid
Furuta, Takashi,Katayama, Motofusa,Shibasaki, Hiromi,Kasuya, Yasuji
, p. 1643 - 1648 (2007/10/02)
An efficient and concise synthesis of three types of multi-labelled histidines with stable isotopes to be used for investigating pharmacokinetics and enzymic reaction mechanisms in vivo is described.Selective deuteriation at C-3 and C-5 of DL-diamino acid 4 was achieved by hydrogen exchange to give DL-diamino acid 5.The imidazole ring was constructed by heating of compound 5 with NaSC(15)N to give labelled 2'-mercapto-DL-histidine 6, which was oxidized at C-2' to give the desired L-histidine L-7 after enzymic resolution.To replace deuterium at C-5' with hydrogen, the labelled histidine was heated in water (pH 5.0) at 180 deg C, and subsequent enzymic resolution gave L-histidine L-8.A similar sequence of reactions carried out on the diamino acid 5 with KS(13)C(15)N gave DL-histidine 7-(13)C.Deuteriation at C-2 and C-2' of 7-(13)C with DCl-D2O (pD 5.0) at 180 deg C and subsequent back-exchange of deuterium at C-2' with water (pH 7.0) at 120 deg C gave DL-histidine 10.Synthesis of optically pure L-histidine starting from L-aspartic acid is also described.The optical purity of the synthesized L-histidine was estimated to be 93.8 percent (e.e).
MONO-ESTERIFICATION OF N-PROTECTED DI-ACIDS ASPARTIC AND GLUTAMIC BY CHLOROFORMATE ACTIVATION
Jouin, P.,Castro, B.,Zeggaf, C.,Pantaloni, A.,Senet, J.P,et al
, p. 1665 - 1668 (2007/10/02)
Mono-esters of N-protected di-acids aspartic and glutamic are prepared by a one-pot activation with alkyl chloroformates or isopropenyl chloroformate and an additionnal alcohol.This process involves the intermediate internal anhydride formation.
