Vol.11 Issue 2 / Latest topics 5Revolution in Predicting Previously Undetermined Structures of Organic Compounds
Our daily lives are overflowing with organic compounds all around us,such as in foods, pharmaceuticals, plastics, detergents, and cosmetics.The characteristics of those compounds vary significantly depending on the number and position of carbon-carbon double bonds. The position of carbon double bonds was previously difficult to determine, such as in lipid research, but oxygen attachment dissociation (OAD), an ion dissociation technology developed by Shimadzu, now enables the position of carbon double bonds to be inferred. The following describes the OAD-TOF system, an analytical solution expected to cause revolutionary changes in society in the near future with technology developed for the first time in the world at the Koichi Tanaka Mass Spectrometry Research Laboratory.
From Conventional Constraints to Cutting-Edge Innovations
With conventional mass spectrometry technology, it was sometimes difficult to analyze the structures of compounds in detail. In particular,determining the position of carbon鈥揷arbon double bonds while retaining the native structure of lipids and other complex organic compounds was challenging. Due to the demand for more detailed structural information in chemical and biotechnology fields, there was an urgent need to develop new technology for structural analysis. The Koichi Tanaka Mass Spectrometry Research Laboratory at Shimadzu Corporation developed OAD technology that can use oxygen radicals to dissociate double bonds between carbons specifically. That OAD technology enables detailed structural analysis that was difficult to achieve with conventional methods. Using cutting-edge mass spectrometry research results, the laboratory provided support throughout the OAD development process from basic research to product commercialization. The typical technique used for structural analysis of molecules in samples by mass spectrometry involves ionizing the target molecule and colliding it with an inert gas, such as argon, referred to as collision-induced dissociation (CID), and then analyzing the dissociated ion fragments. CID is widely used as a generic technique, but it can result in some parts of molecules not dissociating, which can prevent obtaining sufficient structural information for analyzing some targets, such as post-translational modifications of proteins. In response, the Koichi Tanaka Mass Spectrometry Research Laboratory developed the world鈥檚 first technique for fragmenting ions by inducing direct collisions between the ions and highly reactive atomic hydrogen (hydrogen radicals) or atomic oxygen (oxygen radicals). Both the hydrogen attachment/abstraction dissociation (HAD) method, which uses hydrogen radicals, and the oxygen attachment dissociation (OAD) method, which uses oxygen radicals, have attracted significant interest as revolutionary technologies that provide extensive information useful for structural analysis of biological samples.
Diverse Applications of OAD Technology
In December 2023, Shimadzu Corporation released the OAD-TOF quadrupole time-of-flight mass spectrometer system based on those key technologies, the first system in the world to achieve detailed structural analysis of lipids and other natural compounds. By using Shimadzu鈥檚 unique OAD ion dissociation technology to infer the positions of carbon double bonds, which was previously difficult to do, by measuring the size and quantity of sample substances separated down to the atomic and molecular level, and by using that information in combination with accurate compound information obtained with a quadrupole time-of-flight mass spectrometer (Q-TOF MS) system, structures can be identified in lipids, natural substances, and a wide variety of other compounds.
Dual fragmentation via collision-induced and oxygen attachment dissociations using water and its radicals for C=C position-resolved lipidomics
Examples of Using the Product/Technology
鈥� Lipid Analysis: OAD technology is especially useful for determining the positions of carbon double bonds in lipids. Consequently, it has helped provide new knowledge about the functions and activity of lipids, which has been useful for developing new drugs and diagnosing diseases. Example: Analyzing the positions of lipid double bonds in mouse liver In this example, detailed structural information was obtained from a single analysis of lipids contained in a mouse liver extract.
鈥� Structural Analysis of Organic Compounds: The ability to perform detailed structural analysis of complex organic compounds contributes to the development of new functionally beneficial compounds and clarification of biological phenomena. Example: Analyzing the positions of triacylglycerol double bonds in butter This is an example of quickly analyzing the positions of triacylglycerol (TG) double bonds in butter.
Feedback and Future Developments Across Various Fields and Industries
At the International Mass Spectrometry Conference 2024 (IMSC 2024) Shimadzu gave an oral presentation on some of the latest OAD applications.It was introduced that the functionality for analyzing OAD spectra was included in MS-DIAL 5 data analysis software*1 developed by Professor Tsugawa of Tokyo University of Agriculture and Technology,and the functionality can be used for lipid profiling or automatic analysis of lipid structural isomers. Attendees showed particular interest in the broad applicability of the automatic data analysis workflow using MS-DIAL 5 to automatically analyze OAD spectra without changing any pretreatment or chromatography settings and the higher sensitivity achieved by the OAD method compared to other techniques. Professor O鈥橦air鈥檚 group from the University of Melbourne gave a presentation on technology for structural analysis of PFOA-related compounds using OAD. It was the first time that OAD was shown to provide product ions from PFOA-related compounds based on a different dissociation mechanism than CID. That resulted in many questions and comments from many participants involved in environmental analysis or predicting the structures of complex compounds, such as branched chains, and stimulated an exchange of views about possible application fields. Shimadzu remains committed to continue contributing to research advancements in healthcare and life science fields by offering new products.
‘I felt you did: I don’t know why,’ she said. Life on a steamship at sea has many peculiarities. The ship is a world in itself, and its boundaries are narrow. You see the same faces day after day, and on a great ocean like the Pacific there is little to attract the attention outside of the vessel that carries you. You have sea and sky to look upon to-day as you looked upon them yesterday, and will look on them to-morrow. The sky may be clear or cloudy; fogs may envelop you; storms may arise, or a calm may spread over the waters; the great ship goes steadily on and on. The pulsations of the engine seem like those of the human heart; and when you wake at night, your first endeavor, as you collect your thoughts, is to listen for that ceaseless throbbing. One[Pg 53] falls into a monotonous way of life, and the days run on one after another, till you find it difficult to distinguish them apart. The hours for meals are the principal hours of the day, and with many persons the table is the place of greatest importance. They wander from deck to saloon, and from saloon to deck again, and hardly has the table been cleared after one meal, before they are thinking what they will have for the next. The managers of our great ocean lines have noted this peculiarity of human nature; some of them give no less than five meals a day, and if a passenger should wish to eat something between times, he could be accommodated. Another condition of apprenticeship that is equally as difficult to define as the commercial value of mechanical knowledge, or that of apprentice labour, is the extent and nature of the facilities that different establishments afford for learners. Bang! The shutter was closed again. But I did not give it up, for I needed the sisters' assistance to find a shelter somewhere. Once more I made the bell to clang, and although I was kept waiting a little longer, at last I heard voices whispering behind the gate and once more something appeared behind the trellis. Such a view was essentially unfavourable to the progress of science, assigning, as it did, a higher dignity to meagre and very questionable abstractions than to the far-reaching combinations by which alone we are enabled to unravel the inmost texture of visible phenomena. Instead of using reason to supplement sense, Aristotle turned it into a more subtle and universal kind of sense; and if this disastrous assimilation was to a certain extent imposed upon him by the traditions of Athenian thought, it harmonised admirably with the descriptive and superficial character of his own intelligence. Much was also due to the method of geometry, which in his time had already assumed the form made familiar to us by Euclid’s Elements. The employment of axioms side by side with definitions, might, indeed, have drawn his attention to the existence and importance of judgments which, in Kantian terminology, are not analytic but synthetic—that is, which add to the content of a notion instead of simply analysing it. But although he mentions axioms, and states that mathematical theorems are deduced from them, no suspicion of their essential difference from definitions, or of the typical significance which they were destined to assume in the theory of reasoning, seems ever to have crossed his mind; otherwise he could hardly have failed to ask how we come by our knowledge of them, and to what they correspond in Nature. On the whole,385 it seems likely that he looked on them as an analysis of our ideas, differing only from definition proper by the generality of its application; for he names the law of contradiction as the most important of all axioms, and that from which the others proceed;277 next to it he places the law of excluded middle, which is also analytical; and his only other example is, that if equals be taken from equals the remainders are equal, a judgment the synthetic character of which is by no means clear, and has occasionally been disputed.278 387 We have now reached a point where Greek philosophy seems to have swung back into the position which it occupied three hundred years before, towards the close of the Peloponnesian War. The ground is again divided between naturalists and humanists, the one school offering an encyclopaedic training in physical science and exact philology, the other literary, sceptical, and limiting its attention to the more immediate interests of life; but both agreeing in the supreme importance of conduct, and differing chiefly as to whether its basis should or should not be sought in a knowledge of the external world. Materialism is again in the ascendant, to this extent at least, that no other theory is contemplated by the students of physical science; while the promise of a spiritualistic creed is to be found, if at all, in the school whose scepticism throws it back on the subjective sphere, the invisible and impalpable world of mind. The attitude of philosophy towards religion has, indeed, undergone a marked change; for the Stoic naturalists count themselves among the159 most strenuous supporters of beliefs and practices which their Sophistic predecessors had contemned, while the humanist criticism is cautiously guarded by at least an external conformity to established usage; but the Platonic doctrine of immortality has disappeared with the dogmatic spiritualism on which it rested; and faith in superior beings tends to dissociate itself from morality, or to become identified with a simple belief in the fixity of natural law. One temple to Buddha only, on an elongated plan, ends in a vault forming a bulb-shaped cupola supported on massive columns, quite Byzantine in character and wholly unexpected. The dim light, coming in only through a low door and two small windows filled in with pierced carving, enhances the impression of being in some ancient European fane, and the Buddha on the high altar has a look of suffering and emaciation that suggests a work of the fourteenth century. The man was dressed in blue and silver, his belt studded with four-anna pieces; hanging to his girdle was a whole array of small knives, sheaths, and boxes. With his sleeves turned up to his elbows, he fairly amazed me, conjuring away into the air eight rupees that filled his hand, and finding them again one by one in our pockets, bags, or plaids. He turned everything topsy-turvy, swaggered as if he were the master, and then went off, with his broad smile, to amuse other travellers. “Well,” Sandy grinned, “the chewing gum disappeared! Supposing the fellow we thought we saw vanishing really was there and got out some way. He’d know, from Jeff landing us and our going in, that the amphibian might not be usable when he’d need it——” She reloaded for him, and fired from time to time herself, and he moved from the little round hole in the wall to one in the window blind, in the feeble, the faithless hope that the Indians might perhaps be deceived, might fancy that there was more than the one forsaken man fighting with unavailing courage for the quiet woman who stayed close by his side, and for the two children, huddled whimpering in one corner, their little trembling arms clasped round each other's necks. Back of her, a score or more of miles away, were the iron-gray mountains; beyond those, others of blue; and still beyond, others of yet fainter blue, melting into the sky and the massed white clouds upon the horizon edge. But in front of her the flat stretched away and away, a waste of white-patched soil and glaring sand flecked with scrubs. 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