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CC BY-ND-NC 4.0 · Synlett 2019; 30(03): 263-274
DOI: 10.1055/s-0037-1611063
DOI: 10.1055/s-0037-1611063
account
Chlorophyll Breakdown – How Chemistry Has Helped to Decipher a Striking Biological Enigma
Further Information
Publication History
Received: 07 August 2018
Accepted after revision: 20 September 2018
Publication Date:
31 October 2018 (online)
Dedicated to Professor Franz-Peter Monforts on the occasion of his 70th birthday.
Abstract
How the fall colors arise and how chlorophyll (Chl) breakdown occurs in higher plants has remained enigmatic until three decades ago. Fundamental insights into this fascinating puzzle have been gained, meanwhile, by basic contributions from plant biology and chemistry. This short review is a personal account of key advances from synthetic, mechanistic, and structural chemistry that led to the discovery of the bilin-type Chl catabolites and helped elucidate the metabolic processes that generated them from Chl.
1 Introduction
2 Discovery and Structure Elucidation of a First Non-Green Chl Catabolite
3 Structure Elucidation of Fleetingly Existent Blue-Fluorescent Chl Catabolites
4 The Red Chl Catabolite – Key Ring-Opened Tetrapyrrole Accessed by Partial Synthesis
5 Synthesis of ‘Primary’ Fluorescent Chl Catabolites by Reduction of Red Chl Catabolite
6 Nonfluorescent Chl Catabolites from Isomerization of Fluorescent Chl Catabolites
7 Persistent Fluorescent Chl Catabolites and Blue-Luminescent Bananas
8 Discovery, Structure Elucidation, and Biological Formation of Dioxobilin-Type Chl Catabolites
9 Occurrence, Partial Synthesis, and Structure of Phyllochromobilins, the Colored Bilin-Type Chl Catabolites
10 Conclusion and Outlook
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