- Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins
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Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.
- Cai, Yue-Ming,Martin, Ruben,Rui, Xi-Yan,Shang, Ming,Sun, Shang-Zheng,Wang, Jia-Bao,Yao, Hong-Qing,Zhang, De-Liang
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supporting information
p. 1130 - 1137
(2022/02/05)
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- Pillar[5]arene-Based Polycationic Glyco[2]rotaxanes Designed as Pseudomonas aeruginosa Antibiofilm Agents
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Pseudomonas aeruginosa (P.A.) is a human pathogen belonging to the top priorities for the discovery of new therapeutic solutions. Its propensity to generate biofilms strongly complicates the treatments required to cure P.A. infections. Herein, we describe the synthesis of a series of novel rotaxanes composed of a central galactosylated pillar[5]arene, a tetrafucosylated dendron, and a tetraguanidinium subunit. Besides the high affinity of the final glycorotaxanes for the two P.A. lectins LecA and LecB, potent inhibition levels of biofilm growth were evidenced, showing that their three subunits work synergistically. An antibiofilm assay using a double δlecAδlecB mutant compared to the wild type demonstrated that the antibiofilm activity of the best glycorotaxane is lectin-mediated. Such antibiofilm potency had rarely been reached in the literature. Importantly, none of the final rotaxanes was bactericidal, showing that their antibiofilm activity does not depend on bacteria killing, which is a rare feature for antibiofilm agents.
- Coenye, Tom,De Winter, Julien,Diaconu, Andrei,Fransolet, Maude,Gillon, Emilie,Imberty, Anne,Jimmidi, Ravikumar,Michiels, Carine,Mohy El Dine, Tharwat,Vincent, Stéphane P.
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supporting information
p. 14728 - 14744
(2021/10/12)
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- METHODS OF PREPARING N6-((2-AZIDOETHOXY)CARBONYL)LYSINE
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Disclosed herein are methods of preparing N6-((2-azidoethoxy)carbonyl)lysine, N6-((2-azidoethoxy)carbonyl)-L-lysine, and N6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N2-(tert-butoxycarbonyl)-N6-((2-chloroethoxy)carbonyl)-L-lysinate and tertbutyl N6-((2-azidoethoxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.
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Paragraph 0436-0437
(2021/07/02)
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- IMMUNOSTIMULATING AGENT
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The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an antigen. An immunostimulating agent containing at least one kind of a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.
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Paragraph 1458-1460
(2018/11/21)
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- INHIBITORS OF LYSINE GINGIPAIN
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The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its protease Lysine gingipain (Kgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, as described herein, and pharmaceutically acceptable salts thereof.
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Paragraph 0368-0369
(2016/05/02)
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- Unusual orthogonality in the cleavage process of closely related chelating protecting groups for carboxylic acids by using different metal ions
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Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can easily be introduced by coupling the carboxylic acid and the corresponding amine in the presence of 2-(1Hbenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). In addition to being stable to a whole array of reaction conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise and an orthogonal fashion by applying different metal salts.
- Mundinger, Stephan,Jakob, Uwe,Bannwarth, Willi
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supporting information
p. 1258 - 1262
(2014/04/03)
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- Design, synthesis and preliminary activity evaluation of novel L-lysine derivatives as aminopeptidase N/CD13 inhibitors
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A novel class of L-lysine derivatives as aminopeptidase N (APN) inhibitors was designed and synthesized. Activity evaluation showed that compound C7 (IC50 = 9.6 ± 1.3 μM) and C20 (IC50 = 13.6 ± 1.9 μM) were equivalent to the positive control Bestatin (IC50 = 11.3 ± 1.6 μM).
- Wang, Qiang,Xu, Fuming,Mou, Jiajia,Zhang, Jian,Shang, Luqing,Luan, Yepeng,Yuan, Yumei,Liu, Yingzi,Li, Minyong,Fang, Hao,Wang, Binghe,Xu, Wenfang
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scheme or table
p. 847 - 853
(2011/12/04)
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- HETEROCYCLIC SCAFFOLDS USEFUL FOR PREPARATION OF COMBINATORIAL LIBRARIES, LIBRARIES AND METHODS OF PREPARATION THEREOF
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Disclosed are heterocyclic scaffolds useful, for example, for solid-phase organic synthesis of combinatorial libraries and methods for the preparation thereof. Also disclosed are libraries, including combinatorial libraries, and methods for preparation thereof. Exemplified are the following scaffolds (I):
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Page/Page column 18-19
(2009/04/25)
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- ACE-INHIBITORS HAVING ANTIOXIDANT AND NO-DONOR ACTIVITY
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Multifonctional ACE inhibitor compounds are provided, that combine ACE-inhibiting activity with capability to scavenge superoxide and other reactive oxygen species, and that may further function as nitric oxide donors. The compounds are useful for preventing or treating various disorders, including cardiovascular, and diabetes associated disorders.
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Page/Page column 61; 62
(2010/02/07)
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- Selective nitrolytic deprotection of N-BOC-amines and N-BOC-amino acids derivatives
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The extension of the deprotection procedure using HNO3 in CH2Cl2 to a number of appropriately selected N-BOC-masked amines and derivatives of natural amino acids was investigated. The method was found to work effectively with almost all tested substrates, with the exception of activated aromatic amines and heterocycles which underwent unavoidable faster oxidation. Alanine, phenylalanine, serine and lysine derivatives were efficiently deprotected, as well as dipeptide Ala-Phe, preserving the configuration of the substrates and without affecting copresent Z and ester functions, with a remarkable selectivity towards acid sensitive t-butyl esters. The obtained amino acids esters, isolated and characterized in the form of nitrates salts, proved to be suitable intermediates to be used in peptide synthesis.
- Strazzolini, Paolo,Melloni, Tiziana,Giumanini, Angelo G
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p. 9033 - 9043
(2007/10/03)
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- Synthesis of hexapeptide and tetrapeptide analogues of the immunomodulating peptides
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Two hexapeptide and two tetrapeptide analogues of the bioactive hexapeptides [(Trp/Met/Phe)-Lys-Tyr-(Met/Val)-(Pro/Val)-Met] have been synthesized by incorporating novel peptide isosteres such as 2-isoxazoline, (E)-alkene, and reduced amide isosteres. These immunomodulating hexapeptides are known to stimulate the formation of inositol phosphates in lymphocyte cell lines.
- Lee, Ju Young,Chung, Yong Jun,Bae, Yoe-Sik,Ryu, Sung Ho,Kim, Byeang Hyean
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p. 359 - 365
(2007/10/03)
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- Selective deprotection of phenacyl, benzyl and methyl esters of N-protected amino acids and dipeptides and N-protected amino acids benzyl ester linked to resins with bis(tributyltin) oxide
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Phenacyl, methyl and benzyl esters of various N-α-Boc, N-α-Cbz or N,N-dimethylamino protected amino acids and dipeptides, as well as esters of N-α-protected amino acids linked to Wang and Pam resins have been efficiently and chemoselectively cleaved by bis(tributyltin) oxide in aprotic solvents to give the corresponding carboxylic acids in good yields. Moreover, the absence of racemization during the deprotection has been demonstrated. A limitation of the method is the instability of the N-ε-Fmoc group in the amino acid esters 8 and 10, N-α-Fmoc-L-alanine linked to Wang resin 23 and the Cbz protecting groups in N-α-Boc-N-ε-Cbz-L-lysine benzyl and methyl esters (5 and 7), respectively, and N-α-Cbz-L-alanyl-L-alanine methyl ester 19. In the case of N-α-protected dipeptides, there was no evidence of free amino acid which indicates that the peptide bond is unaffected.
- Salomon, Claudio J.,Mata, Ernesto G.,Mascaretti, Oreste A.
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p. 995 - 999
(2007/10/03)
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- Hybridomas and monoclonal antibodies which specifically bind human basic fibroblast growth factor
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A monoclonal antibody is produced from a cloned hybridoma, and the monoclonal antibody combines specifically with basic fibroblast growth factor (bFGF). Therefore, the monoclonal antibody can be advantageously used for assay reagents on bFGF or for purification of bFGF.
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- Synthesis of Unnatural Amino Acids
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This communication presents efficient synthetic procedures for the D and L isomers of Nα-tert-butyloxycarbonyl-Nε-benzyloxycarbonyl-Nε-isopropyllysine dicyclohexylamine salt (Nα-Boc-Nε-Z-Ilys DCHA salt), the D and L isomers of Nα-tert-butyloxycarbonyl-Nεnicotinoyllysine (Nα-Boc-Niclys), β-(3-quinolyl)-D,L-alanine (3-Quinal), and the resolution into the D and L isomers of 3-Quinal.
- Acosta, C. Kirk,Bahr, Martin L.,Burdett, James E.,Cessac, James W.,Martinez, Rudy A.,et al.
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p. 914 - 934
(2007/10/02)
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- Synthesis of Cairomycin-B, a Novel Bicyclic Peptide Containing Lysine and Aspartic Acid
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Cairomycin-B, a bicyclic peptide antibiotic containing lysine and aspartic acid has been synthesised.Diketopiperazine (5) is first prepared from the compound (3), deprotected and subjected to internal cyclisation using DDC and N-hydroxysuccinimide to yield the title compound (7) in 11 percent yield.All the intermediates and final compounds have been fully characterised.
- Kumar, Arun,Singh, Mahak,Chauhan, V. S.
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p. 230 - 232
(2007/10/02)
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- PHOSPHONAMIDATE COMPOUNDS
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Phosphonamidates of the formula STR1 wherein X is a substituted or unsubstituted imino or amino acid or ester. These compounds possess angiotensin converting enzyme activity and are thus useful as hypotensive agents.
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- INVESTIGATION ON PEPTIDE SYNTHESIS BY FRAGMENT CONDENSATION. PART I. SYNTHESIS OF C1 - C4 FRAGMENT OF SUBSTANCE P IN SOLUTION AND BY THE SOLID PHASE METHOD
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The synthesis of protected tetrapeptide Z3-Arg-Pro-Lys(Z)-Pro-OH corresponding to C1 - C4 fragment of substance P in solution and by the solid phase method has been elaborated.
- Orlowska, Alicja,Drabarek, Stefania
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p. 1893 - 1899
(2007/10/02)
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