Thermoreceptors

Breipohl, W.

doi:10.1007/978-3-662-00989-5_28

Cited by 4 publications

(12 citation statements)

References 119 publications

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“…Thus, HTMU (6), HMMU (7), and HDmPyMU (8), the HONM-based uronium salts, were prepared and tested for peptide synthesis and compared with other uronium/aminium (9)(10)(11)(12)(13)(14) salts currently used in our lab and elsewhere ( Figure 2). HTMU (6) is the tetramethyl derivative and forms part of the group of original Knorr reagents [7] such as N-[(1Hbenzotriazol-1-yl)-(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HBTU, 9), [12] N-[(dimethylamino)-1H-1,2,3-triazolo(4,5-b)pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU, 10), [3,13] and O-[cyano(ethoxycarbonyl)methylidene]amino-1,1,3,3-tetramethyluronium hexafluorophosphate (HOTU, 11).…”

Section: Resultsmentioning

confidence: 99%

“…HTMU (6) is the tetramethyl derivative and forms part of the group of original Knorr reagents [7] such as N-[(1Hbenzotriazol-1-yl)-(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HBTU, 9), [12] N-[(dimethylamino)-1H-1,2,3-triazolo(4,5-b)pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU, 10), [3,13] and O-[cyano(ethoxycarbonyl)methylidene]amino-1,1,3,3-tetramethyluronium hexafluorophosphate (HOTU, 11). [14] HMMU (7) incorporates a morpholino group as a hydrogen-bond acceptor in the uronium part, similarly to 1-{[1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholinomethylene]}methanaminium hexafluorophosphate (COMU, 12), 1-[(dimethylamino)(morpholino)methylene]-1H-benzotriazolium hexafluorophosphate 3-oxide (HDMB, 13), and 1-[(dimethylamino)(morpholino)methylene]-1H- [1,3]triazolo-[4,5-b]pyridinium hexafluorophosphate 3-oxide (HDMA, 14). These reagents have shown superiority to those described previously, as the oxygen in the uronium/ iminium skeleton confers the reagent greater solubility, enhances coupling yields and decreases racemization, thereby allowing the use of only 1 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…www.eurjoc.org tion of the anilide was faster with HMMU (7), followed by HDMA (14) and COMU (12), as extracted from the halftimes (see Footnote of Table 1). The formation rates of the product are shown in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

“…Having obtained these encouraging results with HMMU (7), we undertook a more in-depth study using two previously reported peptide systems in order to examine the configuration retention induced by the new coupling reagents in both solution and solid phase. The novel uronium coupling reagents were tested and compared with other dimethylmorpholino [HDMA (14) and COMU (12)] and tetramethyl [HBTU (9), HATU (10), and HOTU (11)] analogues using these models, which involve [1+1] stepwise and also [2+1] segment coupling: Z-Phg-Pro-NH 2 and Z-Phe-Val-Pro-NH 2 . [16][17][18] Regarding the stepwise coupling of Z-Phg-OH to H-Pro-NH 2 (Phg = α-phenylglycine) in solution to render Z-Phg-Pro-NH 2 , Oxyma-based HOTU (11) and COMU (12) and HONM-based HTMU (6) and HMMU (7) showed a greater conservation of chirality ( Table 2, Entries 5, 7, 11, and 9, respectively) over the benzotriazole-based derivatives HBTU (9) and HATU (10) in the presence of DIEA ( Table 2, Entries 1 and 3, respectively).…”

Section: Resultsmentioning

confidence: 99%

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A Novel Family of Onium Salts Based Upon Isonitroso Meldrum's Acid Proves Useful as Peptide Coupling Reagents

2010

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A new family of uronium salts (HTMU, HMMU, and HDmPyMU) based on isonitroso Meldrum's acid (HONM) are reported as stand-alone coupling reagents. Amide bond formation with the use of these reagents occurred more quickly than that with other uronium salts as a result of the presence of a neighboring group effect with a cyclic structure. Thus, these novel onium salts were often more effective in the acylation of poor nucleophiles and in the control of optical purity

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

A Novel Family of Onium Salts Based Upon Isonitroso Meldrum's Acid Proves Useful as Peptide Coupling Reagents

2010

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“…Formation and degradation of radioactive moniliformin 3 from [2-I4C]acetate[67]. dpm = disintegrations per minute Giberella fujikuroi.…”

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Mycotoxins from Mold Fungi — Weapons of Uninivited Fellow‐Boarders of Man and Animal: Structures, Biological Activity, Biosynthesis, and Precautions

Franck¹

1984

Angew. Chem. Int. Ed. Engl.

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In addition to the antibiotics, mycotoxins represent a second large group of biologically active substances of microbial origin. Over 300 mycotoxins are so far known and can be subdivided into 25 structural types. They are formed by approximately 350 molds of which there are 10000 different strains. As mycotoxin-producing molds tend to spread aggressively on foodstuffs, they can cause epidemic mycotoxicoses.-The mycotoxins have been isolated, their structures determined, and their biological activities investigated; their biosynthesis has now also largely been elucidated. Accordingly, mycotoxins are derived from only three groups of key biogenetic building blocks: polyketides, isopentenyl pyrophosphate, and amino acids. Mycotoxins are mainly non-polar, chemically stable, are formed in high concentrations, and do not contain-unlike antibiotics-any sugars. Mycotoxins display an enormous variety of toxic-pharmacological activities, e.g. liver degradation, hemorrhages, carcinomas. The identification of mycotoxicoses is impeded by their long incubation periods and the fact that the mycotoxins tend to accumulate in the mammalian organism, which means that even very low concentrations in food are a potential danger. The particularly dangerous aflatoxin B1 1 may not exceed a limit in food of 5 ppb (5 pg/kg), which is difficult to control. IntroductionEveryone knows what happens when fruit juice is left to stand unprotected for a few days (Fig. 1). Mold colonies are formed from the germs present in the air, usually Aspergillus and Penicillium species. We then do not feel like drinking the juice, our instinct warns us to be careful, and this is important because many of these fungi produce poisonous metabolic products which are dangerous for man and mammals. These poisonous substances are called mycotoxins.The biological activities of the mycotoxins differ from those of the antibiotics produced against bacteria. The mycotoxins and antibiotics provide the microorganisms with effective means of driving other living organisms away Lecture given at the Universitat Gottingen.[**I Extended and supplemented version of an Adolf Windaus Memorial from their sources of food. In Figure 1 the molds have already won this battle, as man can now no longer enjoy the foodstuff they have covered. Some typical features of mycotoxins and antibiotics are compiled in Table 1. Mycotoxins are synthesized by the rapidly growing, aggressively spreading molds; antibiotics are mostly formed by Streptomycetes. Whereas the Streptomycetes are satisfied with residual substances such as cellulose and chitin, which are difficult to degrade, molds compete with higher organisms for their foodstuffs and fodder. Man and mammals are thus greatly endangered by my cot oxins.Penicillin G and streptomycin are the most important antibiotics, whilst aflatoxin B, 1 is the most dangerous representative of the mycotoxins.The danger posed by the mycotoxins and the diseases they cause, mycotoxicoses, were underestimated for a long time, which is why they are also referred ...

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COMU: A Safer and More Effective Replacement for Benzotriazole‐Based Uronium Coupling Reagents

El‐Faham

Funosas

Prohens

et al. 2009

Chemistry A European J

273

296

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We describe a new family of uronium-type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative--especially ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma)--had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (COMU) performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. COMU also showed a less hazardous safety profile than the benzotriazole-based HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.

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Thermoreceptors

Cited by 4 publications

References 119 publications

A Novel Family of Onium Salts Based Upon Isonitroso Meldrum's Acid Proves Useful as Peptide Coupling Reagents

A Novel Family of Onium Salts Based Upon Isonitroso Meldrum's Acid Proves Useful as Peptide Coupling Reagents

Mycotoxins from Mold Fungi — Weapons of Uninivited Fellow‐Boarders of Man and Animal: Structures, Biological Activity, Biosynthesis, and Precautions

COMU: A Safer and More Effective Replacement for Benzotriazole‐Based Uronium Coupling Reagents

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