94882-75-4Relevant academic research and scientific papers
Straightforward synthesis of fluorinated amino acids by Michael addition of ethyl bromodifluoroacetate to α,β-unsaturated α-amino acid derivatives
Kondratov, Ivan S.,Bugera, Maxym Ya.,Tolmachova, Nataliya A.,Daniliuc, Constantin G.,Haufe, Günter
, p. 100 - 108 (2018/05/09)
Copper-mediated Michael addition of ethyl bromodifluoroacetate to N-protected α,β-unsaturated α-amino acid esters was applied for straightforward synthesis of γ,γ-difluorinated analogues of glutamic acid (compound 1) and glutamine (compound 10). Moreover, a proline-based, sterically constrained analog of γ,γ-difluoroglutamic acid (compound 24) was prepared.
Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid
Malhotra, Rajesh,Dey, Tushar K.,Dutta, Swarup,Basu, Sourav,Hajra, Saumen
, p. 6507 - 6515 (2014/08/18)
First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxyla
An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride
Ramapanicker, Ramesh,Mishra, Roli,Chandrasekaran, Srinivasan
experimental part, p. 123 - 125 (2011/02/24)
Dehydroamino acids are important precursors for the synthesis of a number of unnatural amino acids and are structural components in many biologically active peptide derivatives. However, efficient synthetic procedures for their production in large amounts
An efficient synthesis of dehydroamino acids and dehydropeptides from O-Cbz and O-Eoc derivatives of serine and threonine
Ramesh, Ramapanicker,De, Kavita,Chandrasekaran, Srinivasan
, p. 10534 - 10542 (2008/02/13)
A simple and efficient method for the synthesis of dehydroamino acids from serine and threonine is reported. Various O-Cbz and O-Eoc derivatives of serine and threonine are prepared using CbzCl and EocCl, respectively, and are subjected to an anti-selective elimination on treatment with K2CO3 in DMF at 65 °C to afford dehydroalanine and dehydroamino butyric acid derivatives, respectively, in excellent yields. The high stability of these carbonate derivatives of serine and threonine allows their use in normal peptide synthesis as protected serine and threonine residues. Peptides synthesized by incorporating O-Cbz or O-Eoc derivatives undergo ready elimination under the reported conditions, to give the corresponding dehydropeptides in excellent yields. The reaction conditions are mild enough not to cause the racemization of other stereogenic centers present in the peptide.
ARYLPROPIONAMIDE, ARYLACRYLAMIDE, ARYLPROPYNAMIDE, OR ARYLMETHYLUREA ANALOGS AS FACTOR XIA INHIBITORS
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Page/Page column 162, (2008/06/13)
The present invention provides compounds of Formula (I): Formula (I) or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, L1, M and R11 are as defined herein. The compounds of Formula (I) are selective inhibitors of serine protease enzymes of the coagulation cascade and/or contact activation system; for example thrombin, factor Xa, factor XIa, factor IXa, factor VIIa and/or plasma kallikrein. In particular, it relates to compounds that are selective factor XIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.
Versatile and stereoselective syntheses of orthogonally protected β-methylcysteine and β-methyllanthionine
Narayan, Radha S.,VanNieuwenhze, Michael S.
, p. 2655 - 2658 (2007/10/03)
(Chemical Equation Presented) Lantibiotics are a class of lanthionine (and/or β-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic s
Design and synthesis of cyclic sialyl Lewis X mimetics: A remarkable enhancement of inhibition by pre-organizing all essential functional groups
Tsai,Huang,Wong
, p. 9499 - 9503 (2007/10/03)
Two rigid macrocyclic glycopeptides 1 and 2 were designed to mimic the tetrasaccharide SLe(X) as inhibitors of P-selectin. While compound 1 was found to be 1000-fold more potent than SLe(X) with IC50 = 1 μM, compound 2 was not soluble in water for evaluation of its activity. (C) 2000 Elsevier Science Ltd.
Solid-phase synthesis of dehydroalanine derivatives
Yamada, Masaki,Miyajima, Tadatoshi,Horikawa, Hiroshi
, p. 289 - 292 (2007/10/03)
A novel solid-phase synthetic method for dehydroalanines and dehydropeptides has been developed. Elimination of the sulfone part with concomitant release from the solid support afforded the desired dehydroalanine derivatives. The products were given in good yields and excellent purities.
Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates
Casadei, Maria Antonietta,Moracci, Franco Micheletti,Zappia, Giovanni,Inesi, Achille,Rossi, Leucio
, p. 6754 - 6759 (2007/10/03)
The electrochemical reduction of O2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O2·-/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom ω-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-l,3-oxazm-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the β position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.
Synthesis of all Three Regioisomers of Pyridylalanine
Walker, Michael A.,Kaplita, Khane Pham,Chen, Ti,King, H. Dalton
, p. 169 - 170 (2007/10/03)
Pyridylalanines 4-6, differing from one another by the position of attachment on the heterocyclic ring were synthesized in moderate yield starting from serine and 2-, 3- and 4-bromopyridine respectively.
