Lessons and revelations from biomimetic syntheses

Razzak, Mina; Brabander, Jef K. De

doi:10.1038/nchembio.709

Cited by 118 publications

(70 citation statements)

References 117 publications

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“…[1] While our proficiency in solo bond formation has led to magnificent achievements in total synthesis, [2] even our best efforts appear somewhat feeble when compared with biological systems. [3] Frankly, synthetic chemists are presently working far from our true limits. [4] The argument for a move away from solo bond forming reactions is a simple one: since the organic structures that we target are significantly different from cheap and readily available starting materials, our reliance on a 'one bond at a time' strategy inevitably leads to long synthetic sequences (Fig.…”

Section: Introductionmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Section: Introductionmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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“…A consequent challenge is to develop feasible synthetic technologies to make the libraries. A number of technologies have been developed for chemical syntheses (20), biological syntheses (21)(22)(23), and biomimetic syntheses (24)(25)(26)(27)(28)(29).…”

Section: Discussionmentioning

confidence: 99%

Drug Discovery Inspired by Mother Nature: Seeking Natural Biochemotypes and the Natural Assembly Rules of the Biochemome

Yan

2013

J Pharm Pharm Sci

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Purpose. The Human Genome Project is producing a new biological ‘periodic table’, which defines all genes for making macromolecules (proteins, DNA, RNA, etc) and the relations between genes and their biological functions. We now need to consider whether to initiate a biochemome project aimed at discovering biochemistry’s ‘periodic table’, which would define all molecular parts for making small molecules (natural products) and the relations between the parts and their functions to regulate genes. By understanding the Biochemome, we might be able to design biofunctional molecules based upon a set of molecular parts for drug innovation. Methods. A number of algorithms for processing chemical structures are used to systematically derive chemoyls (natural building blocks) from a database of compounds identified in Traditional Chinese Medicine (TCM). The rules to combine chemoyls for biological activities are then deduced by mining an annotated TCM structure-activity database (ATCMD). Based upon the rules and the basic chemoyls, a chemical library can be biochemically profiled, virtual synthetic routes can be planned, and lead compounds can be identified for a specific drug target. Conclusions. The Biochemome is the complete set of molecular components (chemoyls) in an organism and Biochemomics studies the rules governing their assembly and their evolution, together with the relations between the Biochemome and drug targets. This approach provides a new paradigm for drug discovery that is based on a comprehensive knowledge of the synthetic origins of biochemical diversity, and helps to direct biomimetic syntheses aimed at assembling quasi-natural product libraries for drug screening. This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

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“…6 Another significant goal in natural product synthesis is to provide continuous supply of the natural product for further biological evaluation. 7 Inspired by the MacMillan biosynthetic proposal, our synthesis commenced with a reaction of commercially available cheap starting material riboflavin.…”

Section: Scheme 1 Synthetic Approaches To Hunanamycin a A Rt I C L Ementioning

confidence: 99%