- Stereoselective Synthesis of Protected l - Allo -Enduracididine and l -Enduracididine via Asymmetric Nitroaldol Reaction
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The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l - allo -enduracididine and l -enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l -aspartic acid. The cyclic guanidine of di-Cbz-protected l - allo -enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.
- Doi, Takayuki,Ganesan, A.,Masuda, Yuichi,Ohsawa, Kosuke,Thomas, Carys,Tokunaga, Takuya,Zhao, Hongbin
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supporting information
p. 942 - 948
(2020/03/23)
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- COMPLEX
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PROBLEM TO BE SOLVED: To provide a substance that can be used in a simple quantitative method for desmosines. SOLUTION: In the complex of the present invention, desmosine is bound to a protein directly or via a linking group at the side chain terminal of the 4-position of the pyridine ring of desmosine. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0070-0072
(2019/11/03)
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- Process for preparing deuterated desmosine and derivatives thereof
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There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.
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Page/Page column 6; 7; 10
(2019/05/18)
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- Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives
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Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.
- Takaishi, Tomohiro,Wakisaka, Kyosuke,Vavricka, Christopher J.,Kiyota, Hiromasa,Izumi, Minoru
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p. 2126 - 2134
(2019/04/04)
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- Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups
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Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.
- Watanabe, Daisuke,Suzuki, Rina,Usuki, Toyonobu
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supporting information
p. 1194 - 1197
(2017/03/02)
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- A 10th factor inhibitor and its preparation method and application (by machine translation)
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The invention relates to a 10th factor inhibitor and its preparation and application, the 10th factor inhibitor has the structure of formula I, the invention inhibitors to alpha-amino acid as a template, respectively through the amide, carbamate, or urea to the branched chain is formed by a series of novel structure of the compound, this kind of compound can be effectively with the 10th factor binding, prevent the formation of thrombus. (by machine translation)
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Paragraph 0202; 0203
(2016/10/08)
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- Facile synthesis of urea-and thiocarbamate-tethered glycosyl beta-amino acids
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We describe here an efficient way to synthesize series of new urea- and thiocarbamate-tethered glycosyl β-amino acids under mild conditions. These glycosyl β-amino acids are elaborately designed on the basis of natural N-linked glycosides. They have the same side chain length as natural N-glycosyl amino acid while the main chain is replaced with β-amino acid chain. The linkage is an isostere of natural N-linked bond but exhibits competitive stability to chemical and enzymatic hydrolysis. This facile route is benefit from the choice of the commercially available l-aspartic acid as starting material, which not only provides a β-amino acid moiety, but also the α-carboxy group could be transformed to active isocyanate conveniently and economically. The prospective glycosyl β-amino acids are obtained readily by the reaction of isocyanate with appropriately protected glycosylamines and glycosylthiols.
- Teng, Hanbing,Zhang, Zengwei,Zhou, Yifan,Chen, Zhiyong,Chen, Qi,Liu, Yang,Xu, Wenjin
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p. 71868 - 71872
(2015/09/08)
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- VERSATILE AND STEREOSPECIFIC SYNTHESIS OF GAMMA,DELTA -UNSATURATED AMINO ACIDS BY WITTIG REACTION
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The present invention relates to γ,δ-unsaturated a-amino acids of general formula (I). The present invention also provides a versatile process for the stereospecific synthesis of said compounds of formula (I), involving a Wittig reaction. The present invention also relates to intermediate products of general formulae (II) and (III), as shown below, which are involved in the synthesis of compounds (I).
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Page/Page column 30; 31
(2013/03/28)
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- Stereoselective synthesis of unsaturated and functionalized L-NHBoc amino acids, using wittig reaction under mild phase-transfer conditions
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The stereoselective synthesis of a new amino acid phosphonium salt was described by quaternization of melting triphenylphosphine with the β-iodo NHBoc-amino ester, derived from l-aspartic acid. The deprotection of the carboxylic acid function to afford the phosphonium salt with a free carboxylic acid group was achieved by a palladium-catalyzed desallylation reaction. This phosphonium salt was used in the Wittig reaction with aromatic or aliphatic aldehydes and trifluoroacetophenone, under solid-liquid phase-transfer conditions in chlorobenzene and in the presence of K3PO4 as weak base, to afford the corresponding unsaturated amino acids without racemization. Thus, the reaction with substituted aldehydes allows to graft various functionalized groups on the lateral chain of the amino acid, such as trifluoromethyl, cyano, nitro, ferrocenyl, boronato, or azido. In addition, the reaction of the amino acid Wittig reagent with α,β-unsaturated aldehydes leads to amino acids bearing a diene on the lateral chain. Finally, this amino acid phosphonium salt appears to be a new powerful tool for the preparation of unsaturated and non-proteinogenic α-amino acids, directly usable for the synthesis of customized peptides.
- Remond, Emmanuelle,Bayardon, Jerome,Ondel-Eymin, Marie-Joelle,Juge, Sylvain
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p. 7579 - 7587
(2012/10/29)
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- The synthesis of a chiral β-amino acid derivative by the Grignard reaction of an aspartic acid equivalent
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A novel synthetic route to chiral β-amino acid derivative has been developed by a Grignard reaction of 2,4,5-trifluo- rophenyl magnesium bromide with the Weinreb amide derivative of L-aspartic acid. The aspartic equivalent was synthesised from L-aspartic
- Liu, Feng,Yu, Wansheng,Ou, Wenhua,Xu, Xiaojiong,Ruan, Libo,Wang, Xiaoke,Li, Yiming,Peng, Xijiang,Tao, Xiaohu,Mao, Jun,Wan, Jiaomei,Pan, Xianhua
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experimental part
p. 517 - 519
(2010/12/25)
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- Orthogonally protected glycerols and 2-aminodiols: Useful building blocks in heterocyclic chemistry
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The efficient synthesis of orthogonally protected glycerols, 2-aminopropane-1,3-diols and 2-aminobutane-1,4-diols that can constitute useful tools in heterocyclic chemistry, is reported. These interesting tri-functionalized small synthons were easily prepared from serine or aspartic acid. In addition, these substrates can be readily transformed into their iodide derivatives in very good yields. ARKAT USA, Inc.
- Ollivier, Anthony,Goubert, Marlene,Tursun, Ahmatjan,Canet, Isabelle,Sinibaldia, Marie-Eve
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experimental part
p. 108 - 126
(2010/10/03)
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- Synthesis, characterization and cytolytic activity of α-helical amphiphilic peptide nanostructures containing crown ethers
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Many natural α-helical amphiphilic peptides are known to have lytic activity toward different cells. Herein, we describe the synthesis and the characterization of synthetic α-helical amphiphilic peptide nanostructures containing crown ethers, as well as t
- Boudreault, Pierre-Luc,Voyer, Normand
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p. 1459 - 1465
(2008/02/08)
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- Bodipy-VAD-Fmk, a useful tool to study yeast peptide N-glycanase activity
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In this paper the development of a fluorescent activity based probe, Bodipy-VAD-Fmk, for visualization of yeast peptide N-glycanase is described. The activity based probe is used to assess the efficacy of known and new chitobiose-based electrophilic traps to bind yeast peptide N-glycanase. The Royal Society of Chemistry.
- Witte, Martin D.,Descals, Carlos V.,De Lavoir, Sebastiaan V. P.,Florea, Bogdan I.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.
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p. 3690 - 3697
(2008/10/09)
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- A rapid access to the spiroaminoketal framework
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A convergent and stereoselective synthesis of 1-oxa-7-azaspiro[5.5]undecane is described. This functional new spiroheterocycle is readily available from acetone N,N-dimethylhydrazone via a double alkylation and subsequent spiroannulation process. Georg Thieme Verlag Stuttgart.
- Tursun, Ahmatjan,Aboab, Bettina,Martin, Anne-Sophie,Sinibaldi, Marie-Eve,Canet, Isabelle
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p. 2397 - 2399
(2007/10/03)
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- Reactivity of chiral α-amidoalkylphenyl sulfones with stabilized carbanions. Stereoselective synthesis of optically active 1-aminopyrrolizidine
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Metal enolates and functionalized allylzinc reagents react with optically active α-amidoalkylphenyl sulfones to give N-carbamoylamino derivatives with variable levels of anti diastereoselectivity. Zinc enolates provide comparable results with respect to l
- Giri, Nicola,Petrini, Marino,Profeta, Roberto
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p. 7303 - 7308
(2007/10/03)
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- Structure-activity study of L-amino acid-based N-type calcium channel blockers
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Synthesis and structure-activity relationship (SAR) study of L-amino acid-based N-type calcium channel blockers are described. The compounds synthesized were evaluated for inhibitory activity against both N-type and L-type calcium channels focusing on sel
- Seko, Takuya,Kato, Masashi,Kohno, Hiroshi,Ono, Shizuka,Hashimura, Kazuya,Takimizu, Hideyuki,Nakai, Katsuhiko,Maegawa, Hitoshi,Katsube, Nobuo,Toda, Masaaki
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p. 1901 - 1913
(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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- Difluoromethylene analogues of aspartyl phosphate: The first synthetic inhibitors of aspartate semi-aldehyde dehydrogenase
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The difluoromethylene analogue of aspartyl phosphate 6 has been prepared by the fluoride catalysed coupling of diethyl trimethyisilyldifluoromethyl phosphonate with an appropriate aldehyde followed by Dess-Martin oxidation and deprotection; the deprotected compound inhibited (K1 95 μM) aspartate semi-aldehyde dehydrogenase, a key enzyme involved in bacterial amino acid and peptidoglycan biosynthesis.
- Cox,Hadfield,Belen Mayo-Martin
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p. 1710 - 1711
(2007/10/03)
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- Novel route to the synthesis of hydroxylated pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde. Total synthesis of (+)-preussin
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The thermal cyclization of γ-aminoallylstannane (8) having an aldehyde group gave β-hydroxypyrrolidine derivative (9a) as a sole product. This methodology was applied successfully to the total synthesis of (+)-preussin.
- Kadota, Isao,Saya, Shioko,Yamamoto, Yoshinori
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p. 335 - 348
(2007/10/03)
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- Aspartate Racemization in Synthetic Peptides. Part 2. Tendency to Racemization of Aminosuccinyl Residue
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Aminosuccinyl (Asu) peptides, containing a strained ring system, are very vulnerable to epimerization and, during their formation, even as transients, in the presence of nucleophilic and nonnucleophilic bases, partial epimerization occurs.In the presence
- Schoen, Istvan,Szirtes, Tamas,Rill, Attila,Balogh, Gabor,Vadasz, Zsolt,et al.
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p. 3213 - 3223
(2007/10/02)
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- Synthesis of Stereospecific Deuterium-Labeled Homoserines and Homoserine Lactones
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The syntheses of the stereospecific deuteriated derivatives (2S,4R)- and (2S,4S)-2H>homoserine lactone hydrochlorides, (2S,3R)-2H>- and (2S,3S)-2H2>homoserine lactone hydrochlorides, and (2S,3R,4R)-2H2>- and (2S,3S,4S)-2H3>homoserine lactone hydrochlorides as well as the homoserine derivatives themselves have been synthesized in eight simple steps from the appropriate aspartic acids via a route designed for maximal synthetic versatility.The enantiomeric excesses at carbon 4 of the deuteriated homoserines are R = 78percent (98percent 2H) and S = 82percent (98percent 2H) and at carbon 3 R = 100percent (98percent 2H2) and S = 100percent (95percent2H).
- Ramalingam, Kondareddiar,Woodard, Ronald W.
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p. 1900 - 1903
(2007/10/02)
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