- Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine
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Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.
- Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine
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supporting information
p. 2260 - 2268
(2021/03/04)
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- N(?)-2-Naphthylmethoxymethyl-Protected Histidines: Scalable, Racemization-Free Building Blocks for Peptide Synthesis
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Histidine (His) racemizes with relative ease during peptide synthesis. One strategy to suppress this racemization is to protect the nitrogen atom of the imidazole moiety in His with a suitable protecting group. Among the numerous protecting groups that have already been tested, the p-methoxybenzyloxymethyl (PMBOM) group on the ?-nitrogen atom effectively suppresses the racemization. However, a large-scale synthesis of N(?)-PMBOM-protected derivatives has hitherto been hampered by the requirement of a freshly prepared unstable reagent. Herein we report the synthesis of N(?)-2-naphthylmethoxymethyl (NAPOM)-protected His derivatives, which can be prepared on a gram scale and do not suffer from the aforementioned instability problems. Furthermore, these NAPOM-protected His derivatives suppress the racemization in Boc- A nd Fmoc-based peptide synthesis.
- Torikai, Kohei,Watanabe, Louis A.,Yanagimoto, Ryota
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p. 448 - 453
(2020/04/08)
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- Total Synthesis and Functional Characterization of Selenoneine
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The N-α-trimethyl 2-selenohistidine selenoneine is the selenium isolog of the natural antioxidant ergothioneine. Sulfur-to-selenium substitutions are known to endow proteins and nucleic acids with special activities. In contrast, secondary metabolites tha
- Lim, David,Gründemann, Dirk,Seebeck, Florian P.
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supporting information
p. 15026 - 15030
(2019/09/12)
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- Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction
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A concise synthesis of anserine and related compounds was accomplished by Et-DuPhos-Rh-catalyzed asymmetric hydrogenation of dehydrohistidine derivatives in 2,2,2-trifluoroethanol, which played a key role in improving the yield and selectivity.
- Yamashita, Megumi,Shimizu, Keita,Koizumi, Yasuaki,Wakimoto, Toshiyuki,Hamashima, Yoshitaka,Asakawa, Tomohiro,Inai, Makoto,Kan, Toshiyuki
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p. 2734 - 2736
(2016/11/30)
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- Allylpalladium(II) histidylidene complexes and their application in Z-selective transfer semihydrogenation of alkynes
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We have studied the use of amino acid histidine as a precursor for N-heterocyclic carbene (NHC) ligands. This natural amino acid possesses an imidazole substituent, which makes it an interesting NHC precursor that contains both an acid and an amino functi
- Drost, Ruben M.,Broere, Dani?l L. J.,Hoogenboom, Jorin,De Baan, Simone N.,Lutz, Martin,De Bruin,Elsevier
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p. 982 - 996
(2015/03/04)
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- Synthesis of histidinoalanine: A comparison of β-lactone and sulfamidate electrophiles
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Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-d-serine- β-lactone (6) with Boc-l-His-OMe (5) gave a 2:1 mixture of τ- and π-regioisomers. The sulfamidate 10, derived f
- Taylor, Carol M.,De Silva, Samanthi Thabrew
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experimental part
p. 5703 - 5708
(2011/09/16)
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- Brucella suis histidinol dehydrogenase: Synthesis and inhibition studies of a series of substituted benzylic ketones derived from histidine
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Brucella spp. is the causative agent of brucellosis (Malta fever), which is the most widespread zoonosis worldwide. The pathogen is capable of establishing persistent infections in humans which are extremely difficult to eradicate even with antibiotic therapy. Moreover, Brucella is considered as a potential bioterrorism agent. Histidinol dehydrogenase (HDH, EC 1.1.1.23) has been shown to be essential for the intramacrophagic replication of this pathogen. It therefore constitutes an original and novel target for the development of anti-Brucella agents. In this work, we cloned and overexpressed the HDH-encoding gene from Brucella suis, purified the protein and evidenced its biological activity. We then investigated the inhibitory effects of a series of substituted benzylic ketones derived from histidine. Most of the compounds reported here inhibited B. suis HDH in the lower nanomolar range and constitute attractive candidates for the development of novel anti-Brucella agents.
- Abdo, Marie-Rose,Joseph, Pascale,Boigegrain, Rose-Anne,Liautard, Jean-Pierre,Montero, Jean-Louis,Koehler, Stephan,Winum, Jean-Yves
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p. 4427 - 4433
(2008/03/13)
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- HClO4-SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines
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Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be a new, highly efficient, inexpensive and reusable catalyst for chemoselective N-tert-butoxycarbonylation of amines at room temperature and under solvent-free conditions. The Royal Society of Chemistry 2006.
- Chakraborti, Asit K.,Chankeshwara, Sunay V.
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p. 2769 - 2771
(2008/03/28)
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- Deprotection of heteroaromatic carbamates via a base-catalyzed methanolysis
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A simple and mild method for the deprotection of heteroaromatic carbamates via methanolysis using a catalytic amount of base such as sodium methoxide, DBU, or Verkade's base (proazaphosphatranes) is presented. Carbamate protecting group of an aliphatic amine is not affected under these conditions.
- Shieh, Wen-Chung,Xue, Song,McKenna, Joe,Prasad, Kapa,Repi?, Oljan,Blacklock, Thomas
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p. 5645 - 5648
(2007/10/03)
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- Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines
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Indium(III) bromide and chloride efficiently catalysed the N-tert-butoxycarbonylation of amines with (Boc)2O at room temperature and under solvent-free conditions. Various aromatic, heteroaromatic and aliphatic amines were converted to N-tert-butylcarbamates in excellent yields in short times. Chiral amines, esters of α-amino acids and β-amino alcohols afforded optically pure N-t-Boc derivatives in high yields. The reactions were chemoselective and no competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation were observed. Chemoselective conversion to N-tert-butylcarbamates took place with amino alcohols without any formation of oxazolidinones. Georg Thieme Verlag Stuttgart.
- Chankeshwara, Sunay V.,Chakraborti, Asit K.
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p. 2784 - 2788
(2008/02/05)
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- Rapid and facile Lewis acid catalysed Boc protection of amines
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Efficient Boc protection of amines using (Boc)2O in the presence of a catalytic amount of ZrCl4 (10 mol %) in acetonitrile at room temperature is reported with short reaction times and high yields. Efficient Boc protection of amines was carried out using (Boc)2O in the presence of a catalytic amount of ZrCl4 (10 mol %) in acetonitrile at room temperature. The reaction times are very short and the yields are generally high.
- Sharma,Janardhan Reddy,Sree Lakshmi,Radha Krishna, Palakodety
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p. 6963 - 6965
(2007/10/03)
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- A New and Efficient Synthesis of Unnatural Amino Acids and Peptides by Selective 3,3-Dimethyldioxirane Side-Chain Oxidation
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N-Boc derivatives of Leu, Met, Thr, Trp, and Pro, the properties of which resemble those of the respective α-amino acid residues present in proteins, rapidly oxidize in the presence of 3,3-dimethyldioxirane to give different products depending on the stru
- Saladino, Raffaele,Mezzetti, Maurizio,Mincione, Enrico,Torrini, Ines,Paradisi, Mario Paglialunga,Mastropietro, Gaia
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p. 8468 - 8474
(2007/10/03)
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- The first total synthesis of roquefortine D
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The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o- nitrobenzyl group was utilized for histidine side chain protection, and the cyclization to the diketopiperazine was carried out under mild conditions.
- Chen, Wei-Chuan,Joullie, Madeleine M.
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p. 8401 - 8404
(2007/10/03)
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- On the allyl protection of the imidazole ring of histidine
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The regiospecific synthesis of the N(π)-allyl and the N(τ)-allyl derivatives of N(α)-tert-butoxycarbonyl-histidine is described. The DCC-mediated coupling of N(α)-tert-butoxycarbonyl-N(π)-allyl-(L)-histidine with (L)-prolinamide, used as a lest reaction t
- Malanda Kimbonguila,Boucida,Guibe,Loffet
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p. 12525 - 12538
(2007/10/03)
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- Synthesis of potent inhibitors of histidinol dehydrogenase
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Novel inhibitors of histidinol dehydrogenase are described. The most potent inhibitors, compounds 18 (K(i)* = 4.4 nM) and 19 (K(i)* = 2.9 nM) exploit a hitherto unreported lipophilic binding pocket adjoining the active site. Preliminary SAR data for this pocket are detailed. The electrophilic ketone 6 designed to bind to an active site nucleophile was a considerably weaker inhibitor (IC50 ~ 20 μM).
- Dancer, Jane E.,Ford, Mark J.,Hamilton, Kenneth,Kilkelly, Michael,Lindell, Stephen D.,O'Mahony, Mary J.,Saville-Stones, Elizabeth A.
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p. 2131 - 2136
(2007/10/03)
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- Amino-acids and Peptides. Part 45. The Protection of the Thiol Function of Cysteine and the Imidazole-N of Histidine by the Diphenyl-4-pyridylmethyl Group
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S-(Diphenyl-4-pyridylmethyl)-L-cysteine (1) and its derivatives (2)-(7) have been prepared and used in peptide synthesis.In contrast to the analogous S-trityl group, this protection is stable in acid but it is cleaved readily by zinc-acetic acid, by mercury(II) acetate, by iodine, and by electrolytic reduction.N(Im)-Diphenyl-4-pyridylmethyl-L-histidine derivatives (9)-(13) are also reported; the protecting group is again stable to acid but cleaved by hydrogenolysis, by zinc-acetic acid, and by electrolytic reduction, and it has been used in the synthesis of L-histidyl-L-leucine, -L-phenylalanine, and -glycine.
- Coyle, Susan,Hallett, Allan,Munns, Michael S.,Young, Geoffrey T.
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p. 522 - 528
(2007/10/02)
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