NDLI: The Structure And Synthetic Capabilities Of A Catalytic Peptide Formed By Substrate-Directed Mechanism

Content Provider	Springer Nature Link
Author	Fleminger, Gideon Yaron, Tal Eisenstein, Miriam Bar Nun, Akiva
Copyright Year	2005
Abstract	Previously, we have shown that a small substrate may serve as a template in the formation of a specific catalytic peptide, a phenomenon which might have had a major role in prebiotic synthesis of peptide catalysts. This was demonstrated experimentally by the formation of a catalytic metallo-dipeptide, Cys$_{2}$-Fe$^{2+}$, around o-nitrophenyl β-D-galactopyranoside (ONPG), by dicyandiamide (DCDA)-assisted condensation under aqueous conditions. This dipeptide was capable of hydrolyzing ONPG at a specific activity lower only 1000 fold than that of β galactosidase. In the present paper we use molecular modeling techniques to elucidate the structure of this catalyst and its complex with the substrate and propose a putative mechanism for the catalyst formation and its mode of action as a “mini enzyme”. This model suggests that interaction of Fe$^{2+}$ ion with ONPG oxygens and with two cysteine SH groups promotes the specific formation of the Cys$_{2}$-Fe$^{2+}$ catalyst. Similarly, the interaction of the catalyst with ONPG is mediated by its Fe$^{2+}$ with the substrate oxygens, leading to its hydrolysis. In addition, immobilized forms of the catalyst were synthesized on two carriers – Eupergit C and amino glass beads. These preparations were capable of catalyzing the formation of ONPG from β-D-galactose and o-nitrophenol (ONP) under anhydrous conditions. The ability of the catalyst to synthesize the substrate that mediates its own formation creates an autocatalytic cycle where ONPG catalyzes the formation of a catalyst which, in turn, catalyzes ONPG formation. Such autocatalytic cycle can only operate by switching between high and low water activity conditions, such as in tidal pools cycling between wet and dry environments. Implications of the substrate-dependent formation of catalytically active peptides to prebiotic processes are discussed
Starting Page	369
Ending Page	382
Page Count	14
File Format	PDF
ISSN	01696149
Journal	Origins of Life and Evolution of Biospheres
Volume Number	35
Issue Number	4
e-ISSN	15730875
Language	English
Publisher	Kluwer Academic Publishers
Publisher Date	2005-01-01
Publisher Place	Dordrecht
Access Restriction	Subscribed
Subject Keyword	anhydrous synthesis catalytic peptides iron prebiotic catalysis Organic Chemistry Geochemistry Biochemistry
Content Type	Text
Resource Type	Article
Subject	Medicine Ecology, Evolution, Behavior and Systematics Space and Planetary Science

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