Autocatalysis in Formose Reaction and Formation of RNA Nucleosides

Yassin Aweis Jeilani; Minh Tho Nguyen

doi:10.1021/acs.jpcb.0c07070

ChemInform Abstract: Catalytic Formation of Monosaccharides: From the Formose Reaction Towards Selective Synthesis

ChemInform ◽

10.1002/chin.201443256 ◽

2014 ◽

Vol 45 (43) ◽

pp. no-no ◽

Cited By ~ 1

Author(s):

Irina V. Delidovich ◽

Alexandr N. Simonov ◽

Oxana P. Taran ◽

Valentin N. Parmon

Keyword(s):

Selective Synthesis ◽

Formose Reaction

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Formation of Chiral Structures in UV-Initiated Formose Reaction

Doklady Physical Chemistry ◽

10.1134/s001250161803003x ◽

2018 ◽

Vol 479 (1-2) ◽

pp. 57-60 ◽

Cited By ~ 1

Author(s):

S. V. Stovbun ◽

A. A. Skoblin ◽

A. M. Zanin ◽

V. A. Tverdislov ◽

O. P. Taran ◽

...

Keyword(s):

Formose Reaction ◽

Chiral Structures

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Formose reaction accelerated in aerosol-OT reverse micelles

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.262 ◽

2016 ◽

Vol 12 ◽

pp. 2663-2667 ◽

Cited By ~ 1

Author(s):

Makoto Masaoka ◽

Tomohiro Michitaka ◽

Akihito Hashidzume

Keyword(s):

Reverse Micelles ◽

Water Layer ◽

Major Product ◽

Hexadecyltrimethylammonium Bromide ◽

Interfacial Water ◽

Formose Reaction ◽

Aerosol Ot ◽

Aot Reverse Micelles ◽

Triton X ◽

C Nmr

The formose reaction in reverse micelles of aerosol-OT (AOT), triton X-100 (TX), and hexadecyltrimethylammonium bromide (CTAB) was investigated. Time–conversion data have indicated that the interfacial water layer of AOT reverse micelles is a medium that accelerates formation of glycolaldehyde in the formose reaction. The 13C NMR spectra for the products of the formose reaction using formaldehyde-13C as starting material are indicative of the formation of ethylene glycol as a major product.

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Taming Combinatorial Explosion of the Formose Reaction via Recursion within Mineral Environments

10.26434/chemrxiv.7712225.v1 ◽

2019 ◽

Author(s):

Leroy Cronin ◽

Stephanie Colón-Santos ◽

Geoffrey Cooper

Keyword(s):

Building Blocks ◽

Complex Mixtures ◽

Mineral Surfaces ◽

One Pot ◽

Combinatorial Explosion ◽

Formose Reaction ◽

Product Mixture ◽

Number Of Cycles ◽

Reaction Cycles

One-pot reactions of simple precursors, such as those found in the formose reaction or formamide condensation, continuously lead to combinatorial explosions in which simple building blocks capable of function exist, but are in insufficient concentration to self-organize, adapt, and thus generate complexity. We set out to explore the effect of recursion on such complex mixtures by ‘seeding’ the product mixture into a fresh version of the reaction, with the inclusion of different mineral environments, over a number of reaction cycles. Through untargeted UPLC-HRMS analysis of the mixtures<a> we found that the overall number of products detected reduces as the number of cycles increases, as a result of recursively enhanced mineral environment selectivity, </a>thus limiting the combinatorial explosion. This discovery demonstrates how the involvement of mineral surfaces with simple reactions could lead to the emergence of some building blocks found in RNA, Ribose and Uracil, under much simpler conditions that originally thought.

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The favored formation of d,l-arabinitol in the formose reaction

Carbohydrate Research ◽

10.1016/0008-6215(84)85034-x ◽

1984 ◽

Vol 134 (1) ◽

pp. C4-C6 ◽

Cited By ~ 12

Author(s):

Yoshihiro Shigemasa ◽

Akira Matsuba ◽

Nasuo Ueda ◽

Ruka Nakashima ◽

Ken-Ichi Harada ◽

...

Keyword(s):

Formose Reaction

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The Messy Alkaline Formose Reaction and Its Link to Metabolism

Life ◽

10.3390/life10080125 ◽

2020 ◽

Vol 10 (8) ◽

pp. 125

Author(s):

Arthur Omran ◽

Cesar Menor-Salvan ◽

Greg Springsteen ◽

Matthew Pasek

Keyword(s):

Carboxylic Acids ◽

Food Source ◽

Chemical Species ◽

Origins Of Life ◽

Hydroxy Acids ◽

Genetic Elements ◽

Formose Reaction ◽

Alkaline Conditions

Sugars are essential for the formation of genetic elements such as RNA and as an energy/food source. Thus, the formose reaction, which autocatalytically generates a multitude of sugars from formaldehyde, has been viewed as a potentially important prebiotic source of biomolecules at the origins of life. When analyzing our formose solutions we find that many of the chemical species are simple carboxylic acids, including α-hydroxy acids, associated with metabolism. In this work we posit that the study of the formose reaction, under alkaline conditions and moderate hydrothermal temperatures, should not be solely focused on sugars for genetic materials, but should focus on the origins of metabolism (via metabolic molecules) as well.

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