60027-58-9Relevant academic research and scientific papers
The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids
Cerutti, Erika,Viale, Alessandra,Nervi, Carlo,Gobetto, Roberto,Aime, Silvio
, p. 11271 - 11279 (2015/12/01)
A series of dehydroamino acids endowed with different protective groups at the amino and carboxylate moieties and with different substituents at the double bond have been reacted with parahydrogen. The observed ParaHydrogen Induced Polarization (PHIP) effects in the 1H NMR spectra are strongly dependent on the amino protecting group. DFT calculations allowed us to establish a relationship between the structures of the reaction intermediates (whose energies depend on the amido substitution) and the observed PHIP patterns.
Facile formation of dehydroalanine from S-nitrosocysteines
Wang, Hua,Zhang, Jiming,Xian, Ming
supporting information; experimental part, p. 13238 - 13239 (2010/01/30)
(Chemical Equation Presented) A reductive elimination of S-nitrosocysteines using phosphine substrates has been developed. This reaction converts unstable S-nitrosocysteines to dehydroalanine derivatives under very mild conditions. It can potentially be applied for the detection of protein S-nitrosation.
Synthesis of substituted oxazoles from N-acyl-β-hydroxyamino acid derivatives
Ferreira, Paula M. T.,Monteiro, Luis S.,Pereira, Goreti
experimental part, p. 4676 - 4683 (2009/05/27)
Several N-acyl-β-hydroxyamino acids were prepared and treated with di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine, followed by treatment with N,N,N′,N′-tetramethylguanidine to give the corresponding N-acyldehydroamino acids in good
Practical preparation of Z-α-(N-acetylamino)- and Z-α-(N-benzoylamino)-α,β-unsaturated acids
Jursic, Branko S.,Sagiraju, Sarada,Ancalade, Dustin K.,Clark, Traneil,Stevens, Edwin D.
, p. 1709 - 1714 (2008/02/01)
An efficient two-step synthetic procedure for the preparation of numerous variations of N-protected α,β-unsaturated α-amino acids and their corresponding esters from N-protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N-protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base. Copyright Taylor & Francis Group, LLC.
N-Acyl-α-triphenylphosphonioglycinates in the synthesis of α,β-dehydro-α-amino acid derivatives
Mazurkiewicz, Roman,Kuznik, Anna,Grymel, Miroslawa,Kuznik, Nikodem
, p. 807 - 815 (2007/10/03)
N-Acyl-α-triphenylphosphonioglycinates when treated with triethylamine are transformed to an equilibrium mixture of the corresponding N-acyliminoacetates and N-acyl-α-triphenylphosphoranylideneglycinates. Wittig reaction of the latter ylides with aromatic and aliphatic aldehydes or ketones enables a new easy entry to N-acyl-α,β-dehydro-α-amino acid esters. Springer-Verlag 2004.
A short, stereospecific synthesis of dihydrooxazoles from serine and threonine derivatives
Wipf, Peter,Miller, Chris P.
, p. 907 - 910 (2007/10/02)
Cyclization of serine and threonine derivatives with Burgess reagent provides a one-step, streospecific access to 4,5-dihydrooxazoles. Noteworthy features of this new methodology include mild experimental conditions, and the absence of β-lactam, aziridine
NEW SYNTHESES OF α-AMINO ACIDS BASED ON N-ACYLIMINO ACETATES
Bretschneider, Thomas,Miltz, Wolfgang,Muenster, Peter,Steglich, Wolfgang
, p. 5403 - 5414 (2007/10/02)
The reaction of N-acylamino-2-bromoacetates 2 ( via N-acylimino acetates 3 ) with higher order mixed cuprates, trimethylsilyl enol ethers and β-dicarbonyl compounds leads to a variety of α-amino acid derivatives.Their conversion into the free amino acids can be conveniently carried out by the use of t-butyl protection.In case of the N-acetyl compounds cleavage of the protecting group and optical resolution can be achieved in one step hog renal acylase.
α-ALKYLATION OF THREONINE
Seebach, Dieter,Aebi, Johannes, D.
, p. 3311 - 3314 (2007/10/02)
The (S,S)- and the (S,R)-oxazolines 4, both readily available from L-threonine, are deprotonated with lithium diisopropylamide (LDA, -> 5) and alkylated diastereoselectively (>95 percent ds) to yield the 4,4-disubstituted oxazolines 7.The product of methy
N-Acyl Dehydro-α-amino Acids from N-Formyl Dehydro-α-amino Acid Esters
Schoellkopf, Ulrich,Meyer, Rolf
, p. 1469 - 1475 (2007/10/02)
On treatment with methyl potassioisocyanoacetate (2), aldehydes and ketones 1 give N-anionized N-formyl dehydro-α-amino acid methyl esters 3.Compounds 3 with R1 = CH3, R2 = H is obtained by base induced ring opening of methyl 2-oxazoline-4-carboxylate 5. - Acylation of 3, followed by deformation of the intermediates 6, yields N-acyl dehydro α-amino acid methyl esters 7 which can be hydrolyzed to the N-acyl dehydro α-amino-acids 8.
