- Synthesis of novel carboranyl derivatives of α-amino acids
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New routes to closo-carboranyl derivatives of L-lysine and L-glutamic acid with free α-NH2 groups were proposed.
- Gruzdev,Levit,Bazhov,Demin,Sadretdinova,Ol'shevskaya,Kalinin,Krasnov,Chupakhina
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- Analysis of density-dependent binding of glycans by lectins using carbohydrate microarrays
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To investigate the density-dependent binding of glycans by lectins using carbohydrate microarrays, a number of C-terminal hydrazide-conjugated neoglycopeptides with various valences and different spatial arrangements of the sugar ligands were prepared on a solid support. The synthetic strategy includes (1) assembly of alkyne-linked peptides possessing C-terminal hydrazide on a solid support, (2) coupling of azide-linked, unprotected sugars to the alkyne-linked peptides on the solid support utilizing click chemistry, and (3) release of the neoglycopeptides from the solid support. By using this synthetic methodology, sixty five neoglycopeptides with a valency ranging from 1 to 4 and different spatial arrangements of the carbohydrate ligands were generated. Carbohydrate microarrays were constructed by immobilizing the prepared neoglycopeptides on epoxide-derivatized glass slides and were used to analyze the density-dependent binding of glycans by lectins. The results of binding property determinations show that lectin binding is highly dependent on the surface glycan density. Copyright
- Tian, Xizhe,Pai, Jaeyoung,Shin, Injae
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- Synthesis and photochemical reactivity of caged glutamates with a π-extended coumarin chromophore as a photolabile protecting group
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'Caging' and 'uncaging' bioactive substrates are key techniques in studying a wide variety of biological processes. In the present study, two-types of novel caged glutamates with a two-photon absorption (TPA) core, that is, π-extended coumarin, were synthesized and their photochemical release of glutamate was analyzed. The high yields of glutamate (>92%) were observed in the photolysis of compounds 1 and 10, respectively.
- Sakamoto, Yuya,Boinapally, Srikanth,Katan, Claudine,Abe, Manabu
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- TRANSGLUTAMINASE 2 (TG2) INHIBITORS
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Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.
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Paragraph 00321
(2020/03/02)
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- Synthesis of ortho-carboranyl derivatives of (S)-asparagine and (S)-glutamine
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(S)-Asparagine and (S)-glutamine ortho-carboranyl derivatives with free amino and carboxy groups in the α-position were synthesized. By an example of Nγ-(1,2-dicarba-closo-dodecarboran-3-yl)-(S)-glutamine it was demonstrated that the developed synthetic approach carboranyl derivatives of amino acids allowed the preparation of optically pure isomers.
- Gruzdev,Levit,Olshevskaya,Krasnov
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p. 769 - 776
(2017/07/07)
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- LYSINE ISOTOPOLOGUES, COMPOSITIONS COMPRISING THE SAME AND METHODS OF SYNTHESIS
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This invention relates to lysine isotopologues of Formulas I and 1-A, as described herein, and processes for synthesizing the same and derivatives and intermediates involved therein. In one aspect, described herein is a chemical compound comprising an isotopically labeled analog, i.e., an isotopologue of a standard or naturally occurring lysine. The lysine isotopologue is synthetically formed to have stable isotopes of elements incorporated at selected positions. As such, the lysine isotopologue has a molecular mass different from the mass of a standard or naturally occurring lysine.
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- Identification of SNAIL1 Peptide-Based Irreversible Lysine-Specific Demethylase 1-Selective Inactivators
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Inhibition of lysine-specific demethylase 1 (LSD1), a flavin-dependent histone demethylase, has recently emerged as a new strategy for treating cancer and other diseases. LSD1 interacts physically with SNAIL1, a member of the SNAIL/SCRATCH family of transcription factors. This study describes the discovery of SNAIL1 peptide-based inactivators of LSD1. We designed and prepared SNAIL1 peptides bearing a propargyl amine, hydrazine, or phenylcyclopropane moiety. Among them, peptide 3, bearing hydrazine, displayed the most potent LSD1-inhibitory activity in enzyme assays. Kinetic study and mass spectrometric analysis indicated that peptide 3 is a mechanism-based LSD1 inhibitor. Furthermore, peptides 37 and 38, which consist of cell-membrane-permeable oligoarginine conjugated with peptide 3, induced a dose-dependent increase of dimethylated Lys4 of histone H3 in HeLa cells, suggesting that they are likely to exhibit LSD1-inhibitory activity intracellularly. In addition, peptide 37 decreased the viability of HeLa cells. We believe this new approach for targeting LSD1 provides a basis for development of potent selective inhibitors and biological probes for LSD1.
- Itoh, Yukihiro,Aihara, Keisuke,Mellini, Paolo,Tojo, Toshifumi,Ota, Yosuke,Tsumoto, Hiroki,Solomon, Viswas Raja,Zhan, Peng,Suzuki, Miki,Ogasawara, Daisuke,Shigenaga, Akira,Inokuma, Tsubasa,Nakagawa, Hidehiko,Miyata, Naoki,Mizukami, Tamio,Otaka, Akira,Suzuki, Takayoshi
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p. 1531 - 1544
(2016/03/05)
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- Caged glutamates with π-extended 1,2-dihydronaphthalene chromophore: Design, synthesis, two-photon absorption property, and photochemical reactivity
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Caging and photochemical uncaging of the excitatory neurotransmitter l-glutamate (glu) offers a potentially valuable tool for understanding the mechanisms of neuronal processes. Designing water-soluble caged glutamates with the appropriate two-photon absorption property is an attractive strategy to achieve this. This paper describes the design, synthesis, and photochemical reactivity of caged glutamates with π-extended 1,2-dihydronaphthalene structures, which possess a two-photon cross-section of ～120 GM and an excellent buffer solubility (up to 115 mM). High yields up to 99% glutamate were observed in the photolysis of two caged glutamates. Suzuki-Miyaura cross-coupling and Buchwald-Hartwig amination were used as the key reactions to synthesize the caged compounds.
- Boinapally, Srikanth,Huang, Bo,Abe, Manabu,Katan, Claudine,Noguchi, Jun,Watanabe, Satoshi,Kasai, Haruo,Xue, Bing,Kobayashi, Takayoshi
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p. 7822 - 7830
(2015/03/18)
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- Diaminodiacid-based solid-phase synthesis of peptide disulfide bond mimics
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The antimicrobial peptide tachyplesin I was used as a model to apply the title strategy, which was developed for the preparation of peptidic macrocycles with double disulfide surrogates. The folding and activity of the tachyplesin I analogues were found to be sensitive to the structure of the disulfide surrogates, thus underlining the necessity of a flexible synthetic route for generating disulfide bond surrogates with high structural diversity. Copyright
- Cui, Hong-Kui,Guo, Ye,He, Yao,Wang, Feng-Liang,Chang, Hao-Nan,Wang, Yu-Jia,Wu, Fang-Ming,Tian, Chang-Lin,Liu, Lei
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p. 9558 - 9562
(2013/09/23)
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- Inhibition of glyoxalase I: The first low-nanomolar tight-binding inhibitors
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A series of rational modifications to the structure of known S-(N-aryl-N-hydroxycarbamoyl)glutathione-based glyoxalase I inhibitors culminated in the discovery of the first single-digit nanomolar inhibitor. This study makes available key information about possible means to address the issues of metabolic instability, low potency, and synthetic complexicity that have plagued the area of glyoxalase I inhibition. Knowledge garnered from this study has implications in the design of inhibitors with higher conformational definition and lower peptidic character.
- More, Swati S.,Vince, Robert
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supporting information; experimental part
p. 4650 - 4656
(2010/03/01)
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- Design, synthesis, and binding studies of bidentate Zn-chelating peptidic inhibitors of glyoxalase-I
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The known affinity of ethyl acetoacetate (ACC) toward divalent zinc prompted us to attempt its employment as a chelating moiety in the design of glyoxalase-I inhibitors. A practical synthetic route was developed to incorporate this pharmacophore into the side chain of glutamic acid, with flexibility to allow incorporation of additional functionality at the end-stage of the synthesis. Herein, the details of this synthetic approach as well as the evaluation of the resultant β-keto ester compounds are reported.
- More, Swati S.,Vince, Robert
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p. 3793 - 3797
(2008/02/13)
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- Synthesis of protected γ-carboxyglutamates and γ-acylglutamates by rearrangement of N,N-diacylglutamates
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A new method for γ-acylation of protected glutamic acids, involving intramolecular rearrangement of an acyl urethane, has been devised to prepare the protected γ-carboxyglutamates 7, 9 and 11 and the protected 4-acylglutamates 15 and 22 from N,N-bisurethanes or N-acyl-N-urethanes of general structure 1. When the formylurethane 17 was used in the reaction, then the intermediate 18 in the intramolecular rearrangement was obtained. The Royal Society of Chemistry 2005.
- Avent, Anthony G.,Duggan, Heather M. E.,Young, Douglas W.
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p. 2327 - 2332
(2007/10/03)
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- Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties
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Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.
- Barbayianni, Efrosini,Fotakopoulou, Irene,Schmidt, Marlen,Constantinou-Kokotou, Violetta,Bornscheuer, Uwe T.,Kokotos, George
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p. 8730 - 8733
(2007/10/03)
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- Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues
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Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.
- Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan
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p. 5251 - 5253
(2007/10/03)
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- Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation
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We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion). Copyright
- Ohshima, Takashi,Gnanadesikan, Vijay,Shibuguchi, Tomoyuki,Fukuta, Yuhei,Nemoto, Tetsuhiro,Shibasaki, Masakatsu
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p. 11206 - 11207
(2007/10/03)
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- Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases
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Compounds of formula (I) wherein W is —OH or —NHOH; X is an optionally substituted heterocycle, NR1SO2R2, heterocyclylalkythio, CONR2R3or NR1COR2; Y, Z, R1-R3and n are as defined in the application. Compounds (I) are inhibitors of matrix-degrading metalloproteinases and are use for the treatment of related conditions.
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- The synthesis of pyrimidin-4-yI substituted a-amino acids. a versatile approach from alkynyl ketones
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The reaction of amidines with a-amino acid alkynyl ketones is shown to be a versatile route to pyrimidin-4-yl substituted a-amino acids. This route is also applicable to a parallel synthesis approach and has allowed the formation of a range of pyrimidin-4-yl substituted a-amino acids, including the naturally occurring a-amino acid L-lathyrine 4.
- Adlington, Robert M.,Baldwin, Jack E.,Catterick, David,Pritchard, Garcth J.
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p. 855 - 866
(2007/10/03)
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- Total synthesis of the methanogenic cofactors methanofuran and methanofuran b
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Methanofuran, 3-[p-((N-(N″-((4R,5S)- or (4S,5A)-4,5,7-tricarboxyheptanoyl)-γL-glutamyl-γ-L-glutamyl)-β- amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, and methanofuran b, 3-{p-[(N-(-γ-L-glutamyl-γ-L-glutamyl-γ-L-glutamyl-γ-L- glutamyl)-β-amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, are the first cofactors involved in the conversion of carbon dioxide to methane by the methanogenic bacteria Methanobacterium thermoautotrophicum and Methanosarcina barkeri, respectively. These two cofactors have now been synthesized, starting from glutamic acid, dimethyl glutarate, methyl 5-formyl-3-furoate, and tyramine. The synthetic compounds give the same NMR and mass spectra and biological activities as the natural cofactors.
- Sullins, David W.,Bobik, Thomas A.,Wolfe, Ralph S.,Rinehart, Kenneth L.
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p. 6646 - 6651
(2007/10/02)
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