an interesting chirality story: The navy contracted John Frost [0] to make rocket fuel biologically. The normal route to butanetriol (the precursor to butanetrioltrinitrate, BTTN, the rocket fuel in sidewinder missiles) is via reduction of malic acid. In order to do this one must consume large quantities of boron, not terribly hard to obtain in the southwestern US, but the problem is that the partially oxidized borate salts are a bitch to clean up and quite toxic - I guess the Navy wanted a greener way to kill people. A biological route would make the entire process cleaner, and less costly.
The big problem, is of course, that 1,2,4 butanetriol is very much chiral. You might think that because it's gonna basically be burned who cares anyways, but actually since BTTN is a solid rocket propellant, having a different crystal symmetry can cause potentially undesired propellant effects in the bulk. We can't have a rocket that doesn't work, or perhaps worse, occasionally blows up, on the tarmac because of a teeny tiny difference in solid packing geometries.
So Frost had to build two biochemical pathways to the compound. Which he did (btw that is no small feat). The plan was to then combine them 1:1 before subjecting the product to nitration.
Then, just for S&G, they took one enantiomer and nitrated it. Turns out the nitration reaction is harsh enough to quantitatively racemize the compound.
[0] https://patents.google.com/patent/US7923226B2/en
In general, if I were doing biosynthesis for profit, I would probably not want to make anything that didn't have a value-add due to the chiral selectivity.