New polyazaporphine chemistry for the origin of life.
Molecular orbital spectral predictions suggest that 2,5,7,10,12,15,17,20-octaaza-21H, 23H-porphine has a visible spectral range closely matching that of chlorophyll-a. Since the octaazaporphine is, in its core, a simple derivative of an (HCN)12 oligomer, this fact, together with its spectral properties, would suggest that it occupies a high rank as a primordial porphinic solar energy transducer for photochemistry essential to life's formation. The demonstration that the mass 324 hexahydrooctaazaporphine is formed in protic media by the cyclotetramerization of imidazol-4-aminohydroxonium ion or the derived nitrenium ion, and that a mass 318 species consonant with that of the Huckel aromatic octaazaporphine is observed in the course of these studies, strongly supports the proposed octaazaporphine synthesis in a prebiotic hydrocyanic acid milieu.
Neumer
J F
JF
E.I. Du Pont de Nemours & Co., Inc.,  Wilmington, Delaware 19898, USA.
Gordon
M D
MD
McEwen
C N
CN
Peacock
P M
PM
Hill
S A
SA
McKay
R G
RG
Lazar
J
J
Valentine
J R
JR
Van Lenten
F J
FJ
Foris
A
A
D002734:Chlorophyll / Q000737:chemistry; D000077194:Chlorophyll A; D006856:Hydrogen Cyanide / Q000737:chemistry* / Q000528:radiation effects*; D007477:Ions; D017672:Nitrogen Compounds / Q000737:chemistry; D009593:Nitroimidazoles / Q000138:chemical synthesis*; D000069497:Origin of Life; D010777:Photochemistry; D011166:Porphyrins / Q000138:chemical synthesis*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013472:Sunlight
D007477:Ions; D017672:Nitrogen Compounds; D009593:Nitroimidazoles; D011166:Porphyrins; D002734:Chlorophyll; D006856:Hydrogen Cyanide; D000077194:Chlorophyll A