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有机化学界的巨擘-Albert Eschenmoser:a titan of org. chem.

已有 7807 次阅读 2011-12-9 12:46 |系统分类:论文交流| 里程碑, 维生素, Echenmoser有机化学

最近Albert Eschenmoser,一个86岁的老人,在Angewandte chemie上发表一篇论文,长达61页,引文300篇之多,可能是封关之作了:Etiology of Potentially Primordial Biomolecular Structures: From Vitamin B12 to the Nucleic Acids and an Inquiry into the Chemistry of Life's Origin—A Retrospective: 翻译为汉语为:潜在的原生生物分子结构的起源:从维生素B12到核酸-生命起源化学的探析和溯源。(Angew. Chem. Int. Ed. 2011, ASAP)。。

这一篇综述性文章,立意之高足见AE之地位,如果作为一个有机化学人不知道AE的名号,的确应该去科普或者WIKI一下了。。
  AE
的闻名遐迩起始与论文题目中Vitamin B12的全合成,作为有机化学里程碑的工作,Vitamin B12是他与已故的有机合成的教父Robert Woodward共同完成的超级复杂的分子;在一百多个化学者合力下,经过很多年方得以完成;可参见:R. B. Woodward, Pure Appl. Chem. 1968, 17, 519;  1971, 25, 283;1973, 33, 145; “Synthetic Vitamin B12”: R. B.Woodward in Vitamin B12 (Eds.: B. Zagalak, W. Friedrich),Walter de Gruyter, Berlin, 1979, pp. 37–87.
   
一个基本而复杂,并且围绕科学家多少年根本没有解决的天籁之问,生命如何起源?文章首先阐述了经过复杂的自然进化,构建出了复杂而繁多的天然产物分子;天然分子的存在与其结构的生理活性的关联,化学性质与生物性质的关联,及其于生命起源的意义;任何自然选择的先决条件是一个形成分子结构及其相关功能,这两点又是相辅相成的。这两点也是相关化学研究的基石和本质。探究一个原生天然分子往往需要把这两点合二为一;

作者从生命起源化学出发,引申到Vitamin B12说明天然分子骨架的生物形成的多样化和形成缘由。接着引申到简单的核酸结构的化学起源,自然界太多的问号,为什么自然界会选择磷酸作为核酸的功能团?Frank Westheimer从新陈代谢角度说明硫酸酯,硅酸酯,砷酸酯虽然结构上可行,但是功能角度讲,不靠谱。因此溯源研究就是要把结构形成(Formation)和功能(function)结合起来思考和研究。对天然分子的化学结构上的化学测定,与其生物学,物理学的功能性联系起来综合考察,也正正说明了核酸结构可以完美的回答“为什么自然界选择这个,而不是那个”的科学问题。

 

通过该文也可以看到一个有机化学巨擘的研究历程,从全合成转型到生物核酸研究,Albert Eschenmoser 综合了化学和生物学,进行科学方面的探索;另一位Dieter Seebach也是同期的ETH(苏黎世理工大学)的大师,也是从合成化学转型到肽科学方面的研究;

 

Eschenmoser教授在有机化学诸多领域有杰出的科学贡献;从合成方法学到结构解析学,天然产物合成,天然分子的化学起源方面都有建树。The Eschenmoser fragmentation (碎片化反应)the Eschenmoser saltN,N-二甲基亚甲基碘化铵盐),生物基因学的异戊二烯规则的立体化学解释(一种氨的立体化学反转阻碍了对饱和碳的亲核取代;PS,需要自己去读一下,这个规则,我也不是很清楚;isoprene rule http://en.wikipedia.org/wiki/Terpene);AE是寥寥的能作为非美国人而获得美国化学的 The ACS Cope Award 1984)和the Wolf Prize in Chemistry (1986).足见其大师地位。

在该文完成之余,作者还写了Epilogue and Acknowledgement:回顾其科研生涯,算是一个总结。

 

 

The work described in the preceding retrospective summary on an etiology of vitamin B12 and nucleic acid structure has extended over a period of more than three decades. I wish to acknowledge and thank all my former doctoral candidates and postdoctoral associates who, before and after my retirement at ETH, achieved and were co-responsible for the research results described, whether in the Laboratory of Organic Chemistry at the ETH, the Institute for Pharmacy at the University of Frankfurt, or the Scripps Research Institute in La Jolla. I have refrained from listing all my former co-workers due simply to their sheer number, and for this I beg their forgiveness; this applies especially to those whose names do not appear in any of the cited literature, even though their contributions involved no less dedication or commitment. Whenever we failed to achieve a goal in our teaching and learning community—the way I would like to think of our research group —it was ultimately not the fault of the learners, but of the one responsible for setting the goals. With each passing year it has become clearer to me what a privilege it has been to be able to dedicate myself with such a community to pure scientific effort, and to pursue the questions that are the subject of this retrospective. The studies carried out prior to my retirement in 1992 were supported both organizationally and financially by the administration of the ETH ZUrich, the Swiss National Science Foundation, the (former) CIBA Corporation in Basel, as well as Firmenich&Co. in Geneva. After 1992, continued efforts by a small research group at the ETH for more than a decade were made possible thanks to organizational accommodation on the part of my colleagues in the Laboratory of Organic Chemistry, and financial support from the administration of the ETH, the CIBA and Firmenich companies, as well as the newlyestablished Novartis AG. In the years 1994–1997 a part of my research group enjoyed guest privileges at the PharmaceuticalInstitute of the JohannWolfgang-Goethe-Universit_t in Frankfurt. After 1996 the focal point of my research activities shifted to a research group managed jointly with Ram Krishnamurthy in the Skaggs Institute for Chemical Biology at the Scripps Research Institute (TSRI) in La Jolla (California). Our work there was supported financially by the Skaggs Foundation and the administration of TSRI, as well as by NASA. In 2009, I retired again—this time voluntarily. Behind this course of events stands a number of people whom I feel a special obligation to thank. I start with my colleagues Duilio Arigoni and Andrea Vasella, both of whom in the meantime are also retired, in whose former research groups in the organic chemistry laboratory at the ETH after 1992 I was administratively a guest. The magisterial-unconventional help provided to me in those years in large measure by Ralf H_tter, at the time Vice President for Research at the ETH Zurich, I shall not forget. In the late eighties, when the transition from B12 to homo-DNA chemistry demanded from our group a reorientation in working techniques, we may not have succeeded without the help of Christian Leumann.I owe him my special acknowledgment. To two friends, Gerhard Quinkert and Christian Noe, I am indebted for a wonderful period of mutual activity with a group of postdoctoral fellows in the newly-constructed science building at the University of Frankfurt. My very special thanks go out to the President of TSRI, Richard Lerner; my wife Elisabeth and I are deeply grateful for the decision on his part that provided us with an opportunity to experience and enjoy the precious and unforgettable years in California. I wish to include in my thanks the friends and colleagues among the Scripps faculty, with whom I was in close personal and scientific contact over all those years, a contact that to me was precious, reassuring and rejuvenating. Very special appreciation and lasting gratitude are due to my younger colleague at TRSI, Ramanarayanan Krishnamurthy. “Ram” arrived in 1992, after completing doctoral studies at Ohio State University (Prof. David Hart), as a postdoctoral fellow in my newly-formed “post-emeritus”research group at the ETH. He subsequently was a research visitor at SIO in La Jolla as a scientific associate of Gustaf Arrhenius. In

1996 he became the first member,

cofounder, and co-organizer of my

research group at TSRI. He

advanced from research associate

to associate professor at TSRI, and

during the course of thirteen years

whenever I was in Switzerland

rather than in California, Ram looked after my La Jolla

postdoctoral group both scientifically and administratively.

To have been offered in the autumn of my professional life

the collaboration and loyalty of such a humanly endearing,

professionally competent, and intellectually brilliant young

researcher in the person of Ram Krishnamurthy is an extraordinary

gift. Everything that our research group at TSRI

accomplished over the years bears the imprint of his thoughts

and participation, his organizing ability, and his active and

constant concern for everything required for high quality

experimental work by a research group in a chemical

laboratory. In the course of our collaboration, Ram moved

more and more from the role of learner to that of teacher,

becoming a source of skill and knowledge upon which the

other co-workers were able to draw. Since 2009 Ram has been

working with his own independent research group at TSRI.

Finally, I would like to express my gratitude to Dr. William

E. Russey, who translated the German manuscript of this paper

into English. His empathy for the author_s intentions, his

linguistic as well as chemical competence, and his patience with

an author who cannot stop changing a manuscript, made the

collaboration with him a fine and memorable experience.



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