By chemistry standards, the Friedel-Crafts alkylation is a venerable reaction. First reported by chemists Charles Friedel and James Crafts in 1877, the reaction attaches an alkyl substituent to an aromatic ring using an alkyl halide as one of the reactants. It turns out that Nature has been doing this reaction for even longerscientists just didnt know it until now.
Harvard Universitys Emily P. Balskus, Hitomi Nakamura, and Erica E. Schultz have discovered an enzyme, dubbed CylK, that accomplishes this same transformation during the biosynthesis of cylindrocyclophanes, natural products made by cyanobacteria that are toxic to cells (Nat. Chem. Bio. 2017, DOI: 10.1038/nchembio.2421). Because aromatic-alkyl linkages are such important motifs in synthetic compounds, were hoping that the enzyme we found will ultimately be useful for chemical production, says Balskus, who led the research effort.
Her team also found a new type of metal-dependent halogenating enzyme, named CylC, that creates secondary alkyl chlorides. Secondary alkyl halides can be tricky to prepare in the lab because the intermediates en route to making them tend to rearrange. The same can be said for using secondary alkyl halides as reactants in the Friedel-Crafts alkylation.
Secondary alkyl halides have been notoriously problematic substrates for that reaction, Balskus points out. Theyre not very electrophilic, and because the Friedel-Crafts alkylation involves generating a carbocation intermediate, you get a lot of competing side reactions and rearrangements, she says. If we can engineer these enzymes to accept substrates that would be useful building blocks for chemical synthesis, they would fill gaps in our synthetic chemistry toolbox.
Next, Balskus hopes to pin down the mechanisms of the two novel enzymes discovered by her group. X-ray crystal structures of CylC and CylK with bound substrates could be particularly informative, she notes.
Balskus and coworkers have performed an outstanding studyremarkable in its breadth, notable in the novelty of biochemistry encountered, and impactful for its importance to understanding cyanobacterial secondary metabolism as well as biotechnological applications, comments William Gerwick, an expert in the biosynthesis of marine natural products at Scripps Institution of Oceanography.
While much work remains to further characterize both reactions, the current studies place these on a solid biosynthetic foundation, Gerwick continues. This is important, he adds because an informatics analysis of available sequenced cyanobacterial genomes suggests the halogenation to be a highly prevalent mechanism in these organisms and underpins their potential use in biocatalysis applications.
Read the original here:
Chemists discover biology's version of the Friedel-Crafts alkylation - The Biological SCENE
- Howard H. Seliger, Hopkins biology professor - January 1st, 2013 [January 1st, 2013]
- General Biology-Concepts and Investigations - Video - January 31st, 2013 [January 31st, 2013]
- Biology Reproduction part 13 (Sexual reproduction: Flower Structure) CBSE class 10 X - Video - January 9th, 2014 [January 9th, 2014]
- How far can a Buddhist approach to biology take us? - January 14th, 2014 [January 14th, 2014]
- Biology revision song on protein synthesis by Andrew Perkins - Video - January 30th, 2014 [January 30th, 2014]
- Scientific Evidence for Creation CSE BIBLE FORUM Origins 1212 Dr Seuss Biology - Video - February 9th, 2014 [February 9th, 2014]
- Synthetic biology lab backed by 2 million award - April 9th, 2014 [April 9th, 2014]
- Vanguard High teacher wins 2014 Shell Science Lab Challenge - April 9th, 2014 [April 9th, 2014]
- Biohacking and the problem of bioterrorism - April 9th, 2014 [April 9th, 2014]
- Synthetic genetic clock keeps accurate time across a range of temperatures - April 9th, 2014 [April 9th, 2014]
- Math modeling integral to synthetic biology research - April 9th, 2014 [April 9th, 2014]
- Vacancies in biology dept. impact course options - April 9th, 2014 [April 9th, 2014]
- Dr. Joshua Reece Earns Best Presentation Award At Conference - April 9th, 2014 [April 9th, 2014]
- Life Science Reference - Biology Online - April 9th, 2014 [April 9th, 2014]
- 9th Grade Biology: A Hectic Introduction to Mammals - Video - April 9th, 2014 [April 9th, 2014]
- Theism vs Evolution, Biology, and History - Video - April 9th, 2014 [April 9th, 2014]
- AP Biology Ch.49 Circulatory System Livestream - Video - April 9th, 2014 [April 9th, 2014]
- AP Biology Review Cards - Video - April 9th, 2014 [April 9th, 2014]
- AP Biology - Chapter 49 Circulatory System Part 1 - Video - April 9th, 2014 [April 9th, 2014]
- MSc Biology and PhD Boreal Ecology - Video - April 9th, 2014 [April 9th, 2014]
- Whale tales: Students set sail for biology class research - April 10th, 2014 [April 10th, 2014]
- Barnard biology professor honored with Emily Gregory award for teaching - April 10th, 2014 [April 10th, 2014]
- biology: Definition from Answers.com - Answers - The Most ... - April 10th, 2014 [April 10th, 2014]
- Biology - Wikipedia, the free encyclopedia - April 10th, 2014 [April 10th, 2014]
- Bridging the Brain Disease Knowledge Gap through Computational Modeling and Systems Biology: An O... - Video - April 10th, 2014 [April 10th, 2014]
- Sharpening microscope images: New technique takes cues from astronomy, ophthalmology - April 15th, 2014 [April 15th, 2014]
- COLLEGE NEWS: April 13 - April 15th, 2014 [April 15th, 2014]
- Eureka Once, Eureka Twice - April 15th, 2014 [April 15th, 2014]
- Biology - April 15th, 2014 [April 15th, 2014]
- The Art of Nutrients - Biology Song - 'Counting Stars' Remake - Video - April 15th, 2014 [April 15th, 2014]
- Biology - The Nervous System - Video - April 15th, 2014 [April 15th, 2014]
- OCR AS BIOLOGY: - Cell Structures - Video - April 15th, 2014 [April 15th, 2014]
- Evolutionary Biology Research / F. Robin O'Keefe and Julie Meachen / Page Museum - Video - April 15th, 2014 [April 15th, 2014]
- What Is a Thyroid In Biology? : Let's Get Medical - Video - April 15th, 2014 [April 15th, 2014]
- Red Ice Radio - Sofia Smallstorm - Hour 1 - Chemtrails to Pseudo-Life & Synthetic Biology - Video - April 15th, 2014 [April 15th, 2014]
- STARNES: Did professor advocate censorship of conservative student newspaper? - April 15th, 2014 [April 15th, 2014]
- German Research Foundation approves new priority program in the life sciences - April 15th, 2014 [April 15th, 2014]
- Announcing BioCoder issue 3 - April 15th, 2014 [April 15th, 2014]
- Poetry by Linda Bierds, Buddhism and biology - April 15th, 2014 [April 15th, 2014]
- Digestion - Biology Music Video - Video - April 15th, 2014 [April 15th, 2014]
- AS Level Biology- Edexcel/SNAB- Unit 1 Revision Notes - Video - April 15th, 2014 [April 15th, 2014]
- The Anatomy Of The Heart - Video - April 15th, 2014 [April 15th, 2014]
- #OilerNation Biology Program Q & A Hangout - Video - April 15th, 2014 [April 15th, 2014]
- Northwestern University researchers on synthetic biology - Video - April 15th, 2014 [April 15th, 2014]
- Gregor Mendel Institute of Molecular Plant Biology (Vienna) - Video - April 16th, 2014 [April 16th, 2014]
- Biology 1B - 2014-04-14 - Video - April 16th, 2014 [April 16th, 2014]
- AP Biology Review 3/7: Cell Energy - Video - April 16th, 2014 [April 16th, 2014]
- MCB 410: Developmental Biology - Video - April 16th, 2014 [April 16th, 2014]
- Dyslexic Advantage - UCSF Symposium - Dr Fumiko Hoeft - Biology of Stealth Dyslexia - Video - April 16th, 2014 [April 16th, 2014]
- Life cycle of Silkworm- Insect Molecular Biology Lab, Dr.M.Krishnan, Bharathithasan University. - Video - April 16th, 2014 [April 16th, 2014]
- Tracking flu levels with Wikipedia - April 17th, 2014 [April 17th, 2014]
- Biology major Katharine Leigh '15 wins Udall scholarship - April 17th, 2014 [April 17th, 2014]
- First in the nation: UW-Madison establishes post-doc in feminist biology - April 17th, 2014 [April 17th, 2014]
- Biology Project: Predation - Video - April 17th, 2014 [April 17th, 2014]
- Report Focussing On Biology Underlining - Video - April 17th, 2014 [April 17th, 2014]
- edX | MITx: Quantitative Biology Workshop: 7QBWx About Video - Video - April 17th, 2014 [April 17th, 2014]
- Cell Mediated Response (Erdmann's 2B-3 AP Biology) - Video - April 17th, 2014 [April 17th, 2014]
- Biology Plantae part 13 (Mosses: structure, life cycle, mosses vs leafy liverwots) CBSE class 11 XI - Video - April 17th, 2014 [April 17th, 2014]
- Biology - Photosynthesis - Video - April 19th, 2014 [April 19th, 2014]
- The Genie in Your Genes: Epigenetics and Biology of Intention - Video - April 19th, 2014 [April 19th, 2014]
- Introduction to Synthetic Biology Andrew Hessel - Video - April 19th, 2014 [April 19th, 2014]
- Teacher of Biology - April 21st, 2014 [April 21st, 2014]
- Biology - Osmosis - Video - April 21st, 2014 [April 21st, 2014]
- UW to host first feminist biology post-doc program in nation - April 22nd, 2014 [April 22nd, 2014]
- The Biology Project: Cell Biology - University of Arizona - April 22nd, 2014 [April 22nd, 2014]
- The Biology Corner - April 22nd, 2014 [April 22nd, 2014]
- Rader's BIOLOGY 4 KIDS.COM - Biology basics for everyone! - April 22nd, 2014 [April 22nd, 2014]
- Stanford CF Education Day 2014 Understanding the Biology - Video - April 22nd, 2014 [April 22nd, 2014]
- 9th Grade Biology: Hectic Introduction to the Human Organ Systems pt.1 - Video - April 22nd, 2014 [April 22nd, 2014]
- Honors Biology and Biology Mrs. Ellis - Video - April 22nd, 2014 [April 22nd, 2014]
- Biology professor researches parasites - April 22nd, 2014 [April 22nd, 2014]
- TRANSCRIPTION-Biology - Video - April 22nd, 2014 [April 22nd, 2014]
- 2014 Interdisciplinary Innovation Forum: "Mathematical Biology" - Video - April 22nd, 2014 [April 22nd, 2014]
- This Week in Genome Biology - April 24th, 2014 [April 24th, 2014]
- Biology - Calvin Cycle - Video - April 24th, 2014 [April 24th, 2014]
- Systems biology course 2014 Uri Alon - lecture 3: FFL and more - Video - April 24th, 2014 [April 24th, 2014]
- Systems biology course 2014 Uri Alon - lecture 2: Auto regulation - Video - April 24th, 2014 [April 24th, 2014]
- Systems biology course 2014 Uri Alon - lecture 1: Basic concepts - Video - April 24th, 2014 [April 24th, 2014]
- 9th Grade Biology: Hectic Introduction to the Human Organ Systems pt.2 - Video - April 24th, 2014 [April 24th, 2014]
- Have Atheists Hijacked Biology? - Video - April 24th, 2014 [April 24th, 2014]