National Isoprene Appreciation Day .... "Great Things Come in Threes"

I remember in high school reading Shakespeare's Macbeth and noticing how things came in threes. This "things come in threes" trend showed up in his other books as well. 

May 12th (today) is a day when great things come in threes. 

Firstly, today is Mother's Day. I read that the holiday has warped from its original intention/meaning, but that's what things do. They warp. 

Secondly, today is exactly a year since Alex and I started dating, which is pretty crazy for me seeing as how I was convinced I was going to die alone with a thousands dogs. Maybe alone, but certainly not lonely. So much for that fruitless campaign against my own happiness. 

This is a photo from the first day we met. Our first date consisted of a bike ride to Ft. Tilden/Breezy Point/Rockaway (whatever all that space is called), then some exploring around Floyd Bennett Field, appreciating the fuck out of some Black Crowned Night Herons, and finally terminated in him meeting all of my parents' crazy friends at the same time and a lovely walk around Marine Park with Rem. This photo is from the overlook at Ft. Tilden where we happened to meet Luc, a dog who used to come to daycare at the place that I worked. This is back when I refused to make eye contact with anyone who wasn't a dog.

Thirdly, and as Lenny would have you believe, most importantly, I am declaring today National Isoprene Appreciation Day. So what IS Isoprene and why am I so giddy about it?

Terpenes are naturally occuring alkenes. It's a compound whose carbon skeleton is split up into two or more units of isoprene. 

Isoprene has head to tail connections as shown in the above photo. This is the lowest energy connection. 

My organic chem books says the following:

"A study of terpenes provides a glimpse of the wondrous diversity that nature can generate from a simple carbon skeleton. Terpenes also illustrate an important principle of the molecular logic of living systems, namely, that in building large molecules, small units are bonded together enzymatically...."

So just what the in the shit does this mean? The beautiful things we learn from Lenny:

Limonene  is a cyclic terpene - that is to say, it's made up of two isoprene units with head to tail connections, as shown in the above photo. According to Lenny, the R-enantiomer gives orange scent while the S-enantiomer gives lemon scent. I think it's used mostly in cosmetic syntheses to give things nice smells.

Geraniol (coming from ROSES) is used in floral oils and in making perfumes. Look at that fucking structure. Two isoprene units. Head to tail. Not awesome enough for you? Look at retinol. It's a form of Vitamin A and gets bound to the protein opsin. It's ONLY JUST the basis for animal vision. No big deal here, folks. But LOOK at that beautiful structure and those four isoprene units bound, head to tail. Remember, that's the lowest energy connection. We're not looking into breaking bonds there. 

Here's where it gets crazy (for me at least):

That is Beta-carotene. It's something like the primary source of Vitamin A. B-carotene is made up of all of those head to tail connections, and it's symmetrical...in the middle, there is an isoprene TAIL TO TAIL connection. This is a higher energy bond. 

This is what's up: Cleaving that C=C bond gives you vitamin A (Retinol). Retinol is then oxidized to retinal (trans), isomerized by an enzyme to the cis-version of it, which then forms an imine with an -NH2 from a lysine in the protein opsin. This formation gives you Rhodopsin (a pigment that's in the retina), which when it absorbs light, causes dissociation of the retinal from the opsin. Then the whole thing starts over again. 

This is a diagram straight out of the textbook. That big purple glob is the protein opsin. This whole pathway is the first response of the retina to a visual stimulus.

As a heads up, Vitamin E is ALSO made up of 4 isoprene units, in head to tail connections. Shocking stuff, right?

So...I think we should ALL celebrate and appreciate National Isoprene Appreciation Day. Apparently that shit is PRETTY DAMN IMPORTANT. 

As an aside, I now have full capabilities of making eye contact with Alex, not to mention acting like a normal human being. 

See? That's us at my dad's birthday. Like normal human beings. Being real!

:)

Isoprene....represent.