50867-21-5Relevant academic research and scientific papers
The synthesis of (2S)-4,4-difluoroglutamyl γ-peptides based on Garner's aldehyde and fluoro-reformatsky chemistry
Konas, David W.,Pankuch, Jessica J.,Coward, James K.
, p. 2616 - 2626 (2002)
The development of optically active fluorinated synthetic building blocks of general utility is a current goal of organo-fluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of (2S)-4,4-difluoroglutamine, (2S)-4,4-difluoroglutamic acid, and its incorporation into a fluorophore-containing isopeptide 2 designed as a mechanistic probe of γ-glutamyl hydrolase. Compound 2 proved to be a substrate for γ-glutamyl hydrolase and was hydrolyzed at a rate significantly slower than the corresponding non-fluorinated analog.
Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives
Russell, Alexander G.,Sadler, Matthew J.,Laidlaw, Helen J.,Gutierrez-Loriente, Agustin,Wharton, Christopher W.,Carteau, David,Bassani, Dario M.,Snaith, John S.
experimental part, p. 556 - 563 (2012/06/30)
The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.
Inhibitors of protein kinases
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Page/Page column 31, (2011/10/04)
Compounds of general Formula (I): wherein R1, R2, R3, Ra, A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.
4,4-Difluorinated analogues of l-arginine and NG-hydroxy-l-arginine as mechanistic probes for nitric oxide synthase
Martin, Nathaniel I.,Woodward, Joshua J.,Winter, Michael B.,Marletta, Michael A.
supporting information; experimental part, p. 1758 - 1762 (2009/11/30)
4,4-Difluoro-l-arginine and 4,4-difluoro-NG-hydroxy-l-arginine were synthesized and shown to be substrates for the inducible isoform of nitric oxide synthase (iNOS). Binding of both fluorinated analogues to the NOS active site was also investigated using a spectral binding assay employing a heme domain construct of the inducible NOS isoform (iNOSheme). 4,4-Difluoro-NG-hydroxy-arginine was found to bind at the NOS active site in a unique manner consistent with a model involving ligation of the FeIII heme center by the oxygen atom of the NG-hydroxy moiety.
Hydroxylysine containing glycoconjugates: An efficient synthesis of natural galactosylhydroxylysine (Gal-Hyl) and glucosylgalactosylhydroxylysine (Glu-Gal-Hyl) and of their (5S)-epimers
Allevi, Pietro,Paroni, Rita,Ragusa, Andrea,Anastasia, Mario
, p. 3139 - 3148 (2007/10/03)
The paper reports the first chemical synthesis of α-d-glucopyranosyl- (1→2)-β-d-galactopyranosyl-5-O-hydroxylysine, a biological marker of bone resorption and of its unnatural (5S)-epimer, starting from commercial sugars and amino acids. Moreover, the synthetic protocol set-up has resulted in a new procedure for the synthesis of the β-d-galactopyranosyl-5-O- hydroxylysine and its unnatural (5S)-epimer.
Tritiated Peptides. Part 11. Synthesis of 6>-, 11>-, and 6,11>-Somatostatin and the Metabolite 1>-Somatostatin
Allen, Mark C.,Brundish, Derek E.,Martin, John R.,Wade, Roy
, p. 2040 - 2048 (2007/10/02)
The syntheses are described of somatostatin labelled with tritium singly in the phenylalanine residues at positions 6 and 11 and doubly at residues 6 and 11 to specific radioactivities of 15.5, 13.8 and 14.1 Cim mol-1, respectively, by reductive deiodination of fully-protected precursors.Cysteine residues were proteced by S-trityl groups and the disulphide bridge was formed by iodine oxidation of the tritiated protected precursors.The purity of the products was assessed by acidic hydrolysis, ion-exchange and high-pressure liquid chromatography, and by enzymic digestion of the products modified by reduction and aminoethylation.The synthesis of the metabolite 1>-somatostatin is described.The syntheses of 6>-, 11>- and 6,11>-somatostatin are described.
Heteroarylacetamido cephalosporin
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, (2008/06/13)
Novel aminomethyl compounds of the formula STR1 wherein X denotes sulphur or oxygen, R denotes hydrogen or an amino protective group, R1 denotes hydrogen, a free, etherified or esterified hydroxyl group or mercapto group or a substituted ammonium group, R2 denotes hydroxyl or a carboxyl protective radical which together with the carbonyl grouping of the formula -C(=0)- forms a protected carboxyl group, and their salts, are antibacterial antibiotics or intermediates for the preparation thereof; pharmaceutical preparations containing such active compounds, are useful for combating micro-organisms such as gram-positive or gram-negative bacteria; An illustrative example is 3-acetoxymethyl-7β-[2-(5-aminomethyl-2-thienyl)-acetylamino]-ceph-3-em-4-carboxylic acid.
