NEWS & VIEWS RESEARCH para meters of their reactions, including the conditions demanded by industry, or for Manchester M1 7DN, UK. concentrations of the iridium catalyst, the a broad range of substrates, all is not lost. e-mail: [email protected] enzyme and the enzyme’s cofactor. They Techniques such as protein engineering and 1. Rothenberg, G. Catalysis: Concepts and Green developed a system that reduces mixtures directed evolution are increasingly being Applications 2nd edn (Wiley, 2017). of (E)- and (Z)-isomers of alkenes to form a used to rapidly optimize the characteristics of 2. Litman, Z. C., Wang, Y., Zhao, H. & Hartwig, J. F. single stereoisomer, in multi-milligram quan- enzymes (such as their substrate scope, stabil- Nature 560, 355–359 (2018). tities (Fig. 1a). The authors went on to convert ity and selectivity) to make them compatible 3. Rudroff, F. et al. Nature Catal. 1, 12–22 (2018). the stereo isomer into a variety of biologically with industrial processes8. Indeed, enzymes 4. Hönig, M., Sondermann, P., Turner, N. J. & Carreira, E. M. Angew. Chem. Int. Edn 56, active molecules and key intermediates that are the ultimate tunable catalysts, and will 8942–8973 (2017). have been used to prepare such molecules, therefore surely be combined with many other 5. Metternich, J. B. & Gilmour, R. J. Am. Chem. Soc. thereby highlighting the potential applica- chemical catalysts in the future. ■ 137, 11254–11257 (2015). tion of their chemistry for preparative organic 6. Guo, X., Okamoto, Y., Schreier, M. R., Ward, T. R. & Wenger, O. S. Chem. Sci. 9, 5052–5056 (2018). synthesis. Nicholas J. Turner is at the School of 7. Lauder, K. et al. Angew. Chem. Int. Edn 57, As Litman et al. point out, photocatalytic Chemistry, University of Manchester, 5803–5807 (2018). reactions typically occur at or near to room Manchester Institute of Biotechnology, 8. Turner, N. J. Nature Chem. Biol. 5, 567–573 (2009). temperature, which makes them compat- ible with the thermal requirements of enzy- matic systems. Photocatalysts also often work VISION through mechanisms (such as outer-sphere electron transfer and energy transfer) that generate intermediates that are stable in the presence of water and tolerant of the chemical Birds perceive colours groups found in enzymes. Therefore, photo- catalysts in general might be particularly suit- able for being combined with enzymes for in categories synthetic reactions. This compatibility of photo- and enzy- Humans perceive colours in categories such as red, even though we can discern matic processes has been exploited in two red hues including ruby and crimson. It emerges that birds also categorize other studies published earlier this year. In colours and this affects their colour-discrimination ability. See Letter p.365 the first6, a water-soluble iridium catalyst was combined with the enzyme monoamine oxi- dase (MAO-N) to convert racemic mixtures ALMUT KELBER colour-discrimination abilities4, including (one-to-one mixtures of mirror-image stereo- the capacity to perceive the ultraviolet range isomers known as enantiomers) of amine com- he amount of information reaching our of the spectrum. A remarkable earlier study5 pounds into a single enantiomer (Fig. 1b). This sensory organs every second would provided clear evidence that birds can gener- process begins by generating a highly reac- be overwhelming if it were not for our alize among certain colours, and thus divide tive free radical from a starting material (an Tability to categorize it. Colour perception is a the continuum of the colours that they per- imine). The radical is then converted in situ good example of this phenomenon. When we ceive into discrete categories. But it was not to a racemic mixture of amines. MAO-N pick strawberries, we can easily discriminate known whether this ability affects how birds re cycles only one of the enantiomers back between unripe fruit and fruit of the many perceive similar colours and whether it helps into the imine, and the whole process repeats different shades of red that indicate ripeness. them to spot key colour differences. Caves and until all of the imine has been converted into Caves et al.1 report on page 365 that zebra colleagues investigated whether birds’ ability the enantio mer that is not the substrate for finches (Taeniopygia guttata) can also perceive to categorize colours affects their colour- MAO-N. In the second study7, a photo catalytic a continuum of colours as belonging to distinct discrimination abilities, and thus whether reaction of thiols with enones was used to gen- categories, a phenomenon that affects birds’ these animals have erate ketone intermediates that were reduced ability to distinguish similar colours. “Birds are the categorical colour in situ with a ketoreductase enzyme, yielding Although we can easily discriminate only animals, perception. products known as mercaptoalkanols enanti- between the different shades of ripe straw- besides primates, The authors cre- oselectively (Fig. 1c). berries, we tend to generalize and treat these in which ated an ingenious As with all enzymatic systems, the reaction shades as being equivalent. When compar- categorical experimental set-up. scope and scalability of Litman and colleagues’ ing colours, if the differences between them Female zebra finches transformation will determine the extent are on the same scale of separation, our ability colour perception were presented with to which it finds practical applications. For to perceive differences between colours from has now been a device in which example, the alkene substrates reported in two separate categories, say ‘red’ and ‘orange’, demonstrated.” food was hidden the paper are linear molecules that bear aryl is enhanced compared with our ability to per- beneath coloured groups (structural units that contain benzene ceive differences in colours that are both within discs. Food was present beneath bicoloured rings; a substrate bearing an aryl group known one of these categories2,3. This enhanced ability discs and absent below discs composed of a as a pyridine ring is also reported). It will be to distinguish between colours if the colours single colour. This training scheme allowed the interesting to see whether the chemistry can are in separate categories is called categorical authors to test how well the birds recognized be extended to cyclic and non-aryl-bearing colour perception. colour differences by their ability to identify substrates. Moreover, the concentration of sub- The preconditions necessary for the bicoloured discs when searching for food. strates used in the reactions is currently lower ability to perceive colours in distinct catego- The authors studied a range of colours from than would be needed for industrial processes. ries had already been demonstrated in birds. orange to red, evenly dividing this part of the It remains to be seen whether the photo catalyst Humans and our close relatives have evolved spectrum into eight shades of colour. Caves and enzyme will work at industrially useful to have three types of colour-sensing cone and colleagues made great efforts, using physi- substrate concentrations. cell in the eye, and birds have evolved to ological models of bird colour vision, to make Even if the enzyme does not work under have four types4,5. Birds have impressive all of the steps between the shades equivalently ©2018 Spri nger Nature Li mited. All ri ghts reserved. ©2018 Spri nger Nature Li mited. All ri ghts reserved. 16 AUGUST 2018 | VOL 560 | NATURE | 311 RESEARCH NEWS & VIEWS colour categories — is seen only if a subject’s Boundary in language has names for the specific colour cat- a discrimination ability egories being compared2. The other school of thought contends that 1 2 3 4 5 6 7 8 colour perception has a biological basis that is not dependent on cultural and linguistic influences. Evidence to support this view- point includes the observation that terms for specific colours cluster around the same hues b Colours 6 and 8 Colours 5 and 7 across different languages3, and the fact that infants can discriminate between red, green, blue, yellow and purple before they have 3 Bicoloured learnt the words for these colours . Caves discs are and colleagues’ finding that birds have the easier to capacity for categorical colour perception identify Well adds more evidence to support the biological Coloured basis of this phenomenon. disc Why might categorization be important, and how does it fit into the broader context of signal perception? The term ‘categorical perception’ was coined to describe the human Bicoloured ability to distinguish sounds in discrete units, disc Hidden called phonemes, that help to discriminate one seeds word from another (such as the sounds ‘d’, ‘t’, ‘b’ and ‘p’ in the English words bad, bat, pad and pat8). Perception of phoneme-like elements Figure 1 | Categorical colour perception in birds. Caves et al.1 investigated colour perception in also occurs in other animals, including birds9. zebra finches (Taeniopygia guttata). The authors found that, like humans, the birds group colours Categorical perception could be described as into categories and this affects their colour-discrimination ability — a phenomenon called categorical a top-down mechanism to focus on key sen- colour perception. a, The authors tested birds’ ability to distinguish between neighbouring colour sory cues by separating such signals from the pairs in eight evenly separated shades on the orange to red spectrum. Birds were substantially better enormous volume of irrelevant information. at discriminating between shades 5 and 6 than between other pairs, suggesting that this represents a Another way to achieve this separation is a colour-category boundary. b, To test whether birds have the capacity for categorical colour perception, bottom-up approach termed ‘matched filter’, the authors presented birds with a device that had been designed so that the ability to distinguish between two colours and identify bicoloured discs enabled birds to access a food reward.