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What is the most complex molecule we can manufacture without the help of proteins?

This isn't motivated by anything but curiosity about the state of chemical engineering. I realize “complexity” is a loaded term, so I'll defer to the judgment of the respondent: number of molecules, complex arrangement of bonds, or whatever other measure might be appropriate.

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closed as too broad by DSVA, Mithoron, Jon Custer, Todd Minehardt, Oscar Lanzi Aug 1 '17 at 15:14

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    $\begingroup$ "Most complex" isn't well-defined. $\endgroup$ – Ivan Neretin Aug 1 '17 at 14:18
  • $\begingroup$ Complex may not be well-defined, but that doesn't mean it isn't a useful term or that, in most cases, we know it when we see it. Big structures that are simple and repetitive wouldn't, I suggest, count. But even small structures with lots of chiral centres might. $\endgroup$ – matt_black Aug 1 '17 at 15:11
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    $\begingroup$ Oh, and a trivial (and possibly ironic) answer might actually be "proteins" since they can occasionally be synthesised without the use of other proteins. Or possibly DNA/RNA which can be built in stages in the lab as a step towards the biological synthesis of non-natural proteins. $\endgroup$ – matt_black Aug 1 '17 at 15:13
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    $\begingroup$ When I was taking freshman chem the book mentioned that a bowling ball is basically a cross-linked polymer network, so if a "complex molecule" is just a lot of atoms covalently bound together I am going bowling. $\endgroup$ – Oscar Lanzi Aug 1 '17 at 15:18
  • $\begingroup$ If we limit the answer to synthesized chemical substances with a single, definite chemical structure, and apply a generally accepted measure of complexity, then this is an answerable question. For synthetic organic chemists, vitamin B-12 used to be Mt. Everest. $\endgroup$ – iad22agp Aug 1 '17 at 18:43
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I guess in the field of inorganic chemistry polyoxometalates (POMs) are comparable with proteins in terms of structural complexity. Macroanionic POMs such as Keplerates $\ce{\{Mo132\}}$

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are also capable of further self-assembly in diluted solutions, producing so-called "blackberries" [1] of a size of around $\pu{0.05 .. 0.1 \mu m}$:

enter image description here

Also, see the post Measure the complexity of a molecule and the corresponding paper [2] of Prof. Lee Cronin, one of the most productive polyoxometalate chemist of current era.

  1. Kistler, M. L.; Bhatt, A.; Liu, G.; Casa, D.; Liu, T. J. Am. Chem. Soc. 2007, 129 (20), 6453–6460. DOI 10.1021/ja0685809.
  2. Marshall, S. M.; Murray, A. R. G.; Cronin, L. arXiv:1705.03460 [q-bio.OT] 2017.
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