- N-carbamate protected amino acid derived guanidine organocatalysts
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We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poo
- Al-Taie, Zahraa S.,Anderson, Joseph M.,Bischoff, Laura,Christensen, Jeppe,Coles, Simon J.,Froom, Richard,Gibbard, Mari E.,Jones, Leigh F.,de Kleijne, Frank F.J.,Murphy, Patrick J.,Thompson, Emma C.
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- COMPOSITIONS CONTAINING, METHODS AND USES OF ANTIBODY-TLR AGONIST CONJUGATES
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Disclosed herein are Trastuzumab-linked TLR-agonist derivative analogs that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The Trastuzumab-linked TLR-agonist derivative analogs can includ
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Paragraph 00513; 00623; 00628
(2020/08/28)
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- Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides
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The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the constru
- Gro?elj, Uro?,Golobi?, Amalija,Knez, Damijan,Hrast, Martina,Gobec, Stanislav,Ri?ko, Sebastijan,Svete, Jurij
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p. 667 - 676
(2016/07/12)
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- A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
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N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
- Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
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supporting information
p. 10456 - 10460
(2015/11/10)
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- Cu(I)-catalyzed [3+2] cycloadditions of tert-butyl (S)-(3-oxopent-4-yn-2- yl)carbamate to 1-benzylidenepyrazole-3-one-derived azomethine imines
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Parallel screening of suitable reaction conditions for Cu(I)-catalyzed [3+2] cycloadditions of (1Z,4R*,5R*)-4- benzoylamino-1-benzylidene-5-phenyl-3-oxopyrazolidin-1-ium-2-ide (1a) to methyl propiolate (2) has established that this reaction proceeds smoothly at room temperature in acetonitrile in the presence of CuI and Huenig's base. The optimized reaction conditions were then applied in regio- and stereo-selective 1,3-dipolar cycloadditions of racemic azomethine imines 1a-e to tert-butyl (S)-(3-oxopent-4-yn-2-yl)carbamate (6) leading to mixtures of diastereomeric non-racemic chromatographically separable cycloadducts 7a-d, 7′ a-d, 8e, and 8′e. The structures of the products were confirmed by NMR spectroscopy.
- Pusavec, Eva,Mirnik, Jona,Senica, Luka,Groselj, Uros,Stanovnik, Branko,Svete, Jurij
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p. 615 - 626
(2014/06/10)
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- Process development and pilot-plant synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2-yl)cyclopropylamino)propan-2-ylcarbamate: Studies on the scale-up of Kulinkovich-Szymoniak cyclopropanation
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A practical and scalable synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2- yl)cyclopropylamino)propan-2-ylcarbamate, an intermediate in the manufacture of a lymphocyte function-associated antigen 1 inhibitor, is described. The titled compound is prepared via an efficient one-pot, two-step telescoped sequence starting from readily available materials. A modified Kulinkovich-Szymoniak cyclopropanation of a nitrile followed by in situ amide formation with an activated carboxylic acid derivative afforded the target product in about 50% overall isolated yield and >97% purity.
- Li, Wenjie,Gao, Joe J.,Lorenz, Jon C.,Xu, Jinghua,Johnson, Joe,Ma, Shengli,Lee, Heewon,Grinberg, Nelu,Busacca, Carl A.,Lu, Bruce,Senanayake, Chris H.
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experimental part
p. 836 - 839
(2012/08/27)
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- Conversion of α-amino acids into bioactive o-aminoalkyl resorcylates and related dihydroxyisoindolinones
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The synthesis of biologically active o-aminoalkyl resorcylates and related dihydroxyisoindolinones from functionalized α-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.
- Patel, Bhavesh H.,Mason, Andrew M.,Patel, Hetal,Coombes, R. Charles,Ali, Simak,Barrett, Anthony G. M.
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experimental part
p. 6209 - 6217
(2011/10/02)
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- Carbonyldiimidazole (CDI) mediated synthesis of Nα- protected amino acid azides: Application to the one-pot preparation of ureidopeptides
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Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acy
- Vasantha,Vishwanatha,Sureshbabu, Vommina V.
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experimental part
p. 1093 - 1098
(2012/06/01)
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- Chirality transfer in the aza-[2,3]-Wittig sigmatropic rearrangement
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The aza-[2,3]-Wittig sigmatropic rearrangements of substrates derived from enantiomerically pure alanine, valine and serine with phenyl and ester anion stabilising groups were investigated for their efficiency in chirality transfer. It was found that a me
- Anderson, James C.,Gair Ford,Whiting, Matthew
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p. 3734 - 3748
(2007/10/03)
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- Inhibitors of biotin biosynthesis as potential herbicides
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Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR50 (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values 2 showed moderate activity.
- Nudelman, Ayelet,Marcovici-Mizrahi, Dana,Nudelman, Abraham,Flint, Dennis,Wittenbach, Vernon
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p. 1731 - 1748
(2007/10/03)
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- Isolation and Structure Determination of Lyngbyastatin 3, a Lyngbyastatin 1 Homologue from the Marine Cyanobacterium Lyngbya majuscula. Determination of the Configuration of the 4-Amino-2,2-dimethyl-3-oxopentanoic Acid Unit in Majusculamide C, Dolastatin 12, Lyngbyastatin 1, and Lyngbyastatin 3 from Cyanobacteria
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The structure of lyngbyastatin 3 (1), including the configurations of the two unusual amino acid residues, viz., the 3-amino-2-methylhexanoic acid (Amha) and 4-amino-2,2-dimethyl-3-oxopentanoic acid units (Ibu), has been established by chemical degradation. Analysis of the cyanobacterial samples of lyngbyastatin 3 (1), lyngbyastatin 1 (2), and dolastatin 12 (3) demonstrated that they are mixtures of Ibu epimers [R (major) and S (minor)], whereas the structurally related majusculamide C (4) is a single diastereomer having an S-Ibu unit.
- Williams, Philip G.,Moore, Richard E.,Paul, Valerie J.
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p. 1356 - 1363
(2007/10/03)
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- The synthesis of the vitamers of biotin
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An efficient synthetic pathway for the preparation of the vitamers of biotin which provides easy access to optically pure KAPA as well as diastereomeric mixtures of DAPA, DTB, and analogs thereof has been developed.
- Nudelman, Abraham,Nudelman, Ayelet,Marcovici-Mizrahi, Dana,Flint, Dennis
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p. 157 - 168
(2007/10/03)
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- Peptidomimetic inhibitors of the human cytomegalovirus protease
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The development of peptidomimetic inhibitors of the human cytomegalovirus (HCMV) protease showing sub-micromolar potency in an enzymatic assay is described. Selective substitution of the amino acid residues of these inhibitors led to the identification of tripeptide inhibitors showing improvements in inhibitor potency of 27-fold relative to inhibitor 39 based upon the natural tetrapeptide sequence. Small side chains at P1 were well tolerated by this enzyme, a fact consistent with previous observations. The S2 binding pocket of HCMV protease was very permissive, tolerating lipophilic and basic residues. The substitutions tried at P3 indicated that a small increase in inhibitor potency could be realized by the substitution of a tert-leucine residue for valine. Substitutions of the N- terminal capping group did not significantly affect inhibitor potency. Pentafluoroethyl ketones, α,α-difluoro-β-keto amides, phosphonates and α- keto amides were all effective substitutions for the activated carbonyl component and gave inhibitors which were selective for HCMV protease. A slight increase in potency was observed by lengthening the P1' residue of the α-keto amide series of inhibitors. This position also tolerated a variety of groups making this a potential site for future modifications which could modulate the physicochemical properties of these molecules.
- Ogilvie, William,Bailey, Murray,Poupart, Marc-André,Abraham, Abraham,Bhavsar, Amit,Bonneau, Pierre,Bordeleau, Josée,Bousquet, Yves,Chabot, Catherine,Duceppe, Jean-Simon,Fazal, Gulrez,Goulet, Sylvie,Grand-Ma?tre, Chantal,Guse, Ingrid,Halmos, Ted,Lavallée, Pierre,Leach, Michael,Malenfant, Eric,O'Meara, Jeff,Plante, Raymond,Plouffe, Céline,Poirier, Martin,Soucy, Fran?ois,Yoakim, Christiane,Déziel, Robert
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p. 4113 - 4135
(2007/10/03)
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- Synthesis and structure-activity relationships of 7-[3-(1- aminoalkyl)pyrrolidinyl]- and 7-[3-1-aminocycloalkyl)pyrrolidinyl]-quinolone antibacterials
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A series of 7-[3-(1-aminoalkyl and 1-aminocycloalkyl)-1- pyrrolidinyl]quinolones have been prepared and their biological properties evaluated. Among them, 1-(S)-aminoalkyl derivatives exhibited potent antibacterial activities against gram-positive and gram-negative organisms. They had moderate lipophilicity and high aqueous solubility compared to their aminomethyl counterparts; e.g., the 3-(1-aminoethyl)-1-pyrrolidinyl compound (83) showed superior pharmacokinetic properties to its aminomethyl counterpart (6).
- Kimura,Atarashi,Takahashi,Hayakawa
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p. 1442 - 1454
(2007/10/02)
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- Decarboxylative Carbon Acylation of Malonates with Aminoacylimidazoles Mediated by Lewis Acids
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Various N-protected aminoacylimidazoles undergo decarboxylative carbon acylation with sodium or potassium monomethylmalonate in THF in the presence of MgCl2, CoCl2 or MnCl2 to give dipeptide analogues (3) in 45-82percent isolated yield.Amino ketoester (3e) undergoes intramolecular cyclization induced by diisopropylethylamine and anhydrous magnesium chloride to trisubstituted tetramic acid (4).
- Mansour, Tarek S.,Evans, Colleen A.
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p. 773 - 781
(2007/10/02)
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