Synlett 2017; 28(01): 93-97
DOI: 10.1055/s-0036-1588657
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© Georg Thieme Verlag Stuttgart · New York

A Plausible Prebiotic Origin of Glyoxylate: Nonenzymatic Transamination Reactions of Glycine with Formaldehyde

Fiaz S. Mohammeda, Ke Chenb, Mike Mojicab, Mark Conleya, Jonathan W. Napolineb, Christopher Butcha, Pamela Polletb, Ramanarayanan Krishnamurthy*c, Charles L. Liotta*a, b
  • aSchool of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA 30332, USA   Email: charles.liotta@chemistry.gatech.edu
  • bSchool of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA
  • cDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA   Email: rkrishna@scripps.edu
Further Information

Publication History

Received: 26 September 2016

Accepted after revision: 01 November 2016

Publication Date:
17 November 2016 (eFirst)

Abstract

Glyoxylate has been postulated to be an important prebiotic building block. However, a plausible prebiotic availability of glyoxylate has not as yet been demonstrated. Herein we report the formation of glyoxylate by means of a transamination reaction between glycine and formaldehyde in water at 50 °C and 70 °C at pH 8 and 6, respectively. The reaction was followed by means of 13C NMR and high-resolution mass spectrometry employing both unlabeled and 13C-labeled reactants. Other products accompanying the transamination process include serine, sarcosine, N,N-dimethylglycine, and carbon dioxide/bicarbonate. The mechanisms for the formation of glyoxylate and accompanying products are discussed.

1 Introduction

2 Background

3 Results and Discussion

3.1 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 8

3.2 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 6

3.3 Serine-Promoted Decarboxylation of Glyoxylate

4 Conclusions

Supporting Information