Structure and conformation of photosynthetic pigments and related compounds. 15. Conformational analysis of chlorophyll derivatives - implications for hydroporphyrins in vivo

Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a la...

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Published inPhotochemical & photobiological sciences Vol. 18; no. 6; pp. 1479 - 1494
Main Authors Gibbons, Daire, Flanagan, Keith J., Pounot, Léa, Senge, Mathias O.
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 01.06.2019
Royal Society of Chemistry
Subjects
Biochemistry
Biological activity
Biomaterials
Chemistry
Chlorophyll
Chlorophyll - analogs & derivatives
Chlorophyll - chemistry
Cofactors
Conformational analysis
Crystal structure
Derivatives
Mathematical analysis
Molecular Conformation
Molecular structure
Photosynthesis
Photosynthetic pigments
Photosynthetic Reaction Center Complex Proteins - chemistry
Physical Chemistry
Pigmentation
Pigments
Plant Sciences
Porphyrins - chemistry
Reaction centers
Solvents
Tetrapyrroles
Unit cell
Online AccessGet full text
ISSN1474-905X
1474-9092
1474-9092
DOI10.1039/c8pp00500a

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Abstract Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a large role in controlling their biological activity. While there is no small molecule crystal structure of chlorophyll, the normal-coordinate structural decomposition (NSD) method is a very useful analytical tool for conformational analysis of chlorophylls, using tetrapyrroles that mimic their structure. NSD allows for an analysis of the individual macrocyclic distortion modes and their contributions to the overall conformation. Herein, we present our own validation of the NSD program and use it to carry out a conformational analysis of chlorophyll-related compounds. Metal insertions, peripheral substi-tuents, and solvents in the unit cell give rise to different NSD profiles in chlorophyll derivatives. These range from planar and non-planar conformations upon metal insertions, to polar peripheral substituents, and fused rings in chlorins. Substituent effects are clearly evidenced in highly β-substituted chlorins and while bacteriochlorins and isobacteriochlorins experience similar effects to the chlorins, they are also subject to solvent effects, causing the macrocycle to be non-planar. Overall, we report a first conformational analysis of all 'chlorophyll'-related small molecule crystal structures at an atomic level.
AbstractList Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a large role in controlling their biological activity. While there is no small molecule crystal structure of chlorophyll, the normal-coordinate structural decomposition (NSD) method is a very useful analytical tool for conformational analysis of chlorophylls, using tetrapyrroles that mimic their structure. NSD allows for an analysis of the individual macrocyclic distortion modes and their contributions to the overall conformation. Herein, we present our own validation of the NSD program and use it to carry out a conformational analysis of chlorophyll-related compounds. Metal insertions, peripheral substi-tuents, and solvents in the unit cell give rise to different NSD profiles in chlorophyll derivatives. These range from planar and non-planar conformations upon metal insertions, to polar peripheral substituents, and fused rings in chlorins. Substituent effects are clearly evidenced in highly β-substituted chlorins and while bacteriochlorins and isobacteriochlorins experience similar effects to the chlorins, they are also subject to solvent effects, causing the macrocycle to be non-planar. Overall, we report a first conformational analysis of all 'chlorophyll'-related small molecule crystal structures at an atomic level.
Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a large role in controlling their biological activity. While there is no small molecule crystal structure of chlorophyll, the normal-coordinate structural decomposition (NSD) method is a very useful analytical tool for conformational analysis of chlorophylls, using tetrapyrroles that mimic their structure. NSD allows for an analysis of the individual macrocyclic distortion modes and their contributions to the overall conformation. Herein, we present our own validation of the NSD program and use it to carry out a conformational analysis of chlorophyll-related compounds. Metal insertions, peripheral substituents, and solvents in the unit cell give rise to different NSD profiles in chlorophyll derivatives. These range from planar and non-planar conformations upon metal insertions, to polar peripheral substituents, and fused rings in chlorins. Substituent effects are clearly evidenced in highly β-substituted chlorins and while bacteriochlorins and isobacteriochlorins experience similar effects to the chlorins, they are also subject to solvent effects, causing the macrocycle to be non-planar. Overall, we report a first conformational analysis of all 'chlorophyll'-related small molecule crystal structures at an atomic level.
Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a large role in controlling their biological activity. While there is no small molecule crystal structure of chlorophyll, the normal-coordinate structural decomposition (NSD) method is a very useful analytical tool for conformational analysis of chlorophylls, using tetrapyrroles that mimic their structure. NSD allows for an analysis of the individual macrocyclic distortion modes and their contributions to the overall conformation. Herein, we present our own validation of the NSD program and use it to carry out a conformational analysis of chlorophyll-related compounds. Metal insertions, peripheral substituents, and solvents in the unit cell give rise to different NSD profiles in chlorophyll derivatives. These range from planar and non-planar conformations upon metal insertions, to polar peripheral substituents, and fused rings in chlorins. Substituent effects are clearly evidenced in highly β-substituted chlorins and while bacteriochlorins and isobacteriochlorins experience similar effects to the chlorins, they are also subject to solvent effects, causing the macrocycle to be non-planar. Overall, we report a first conformational analysis of all 'chlorophyll'-related small molecule crystal structures at an atomic level.Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well understood on the basis of protein structural data and a significant body of information indicates that the conformation of tetrapyrroles plays a large role in controlling their biological activity. While there is no small molecule crystal structure of chlorophyll, the normal-coordinate structural decomposition (NSD) method is a very useful analytical tool for conformational analysis of chlorophylls, using tetrapyrroles that mimic their structure. NSD allows for an analysis of the individual macrocyclic distortion modes and their contributions to the overall conformation. Herein, we present our own validation of the NSD program and use it to carry out a conformational analysis of chlorophyll-related compounds. Metal insertions, peripheral substituents, and solvents in the unit cell give rise to different NSD profiles in chlorophyll derivatives. These range from planar and non-planar conformations upon metal insertions, to polar peripheral substituents, and fused rings in chlorins. Substituent effects are clearly evidenced in highly β-substituted chlorins and while bacteriochlorins and isobacteriochlorins experience similar effects to the chlorins, they are also subject to solvent effects, causing the macrocycle to be non-planar. Overall, we report a first conformational analysis of all 'chlorophyll'-related small molecule crystal structures at an atomic level.
Author Flanagan, Keith J.
Pounot, Léa
Senge, Mathias O.
Gibbons, Daire
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  givenname: Keith J.
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  givenname: Mathias O.
  surname: Senge
  fullname: Senge, Mathias O.
  email: sengem@tcd.ie
  organization: School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, Trinity College Dublin, the University of Dublin
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30964476$$D View this record in MEDLINE/PubMed
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Snippet Chlorophylls are fundamental macrocyclic cofactors in photosynthetic reaction centers and light-harvesting complexes. Their biological function is well...
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SubjectTerms Biochemistry
Biological activity
Biomaterials
Chemistry
Chlorophyll
Chlorophyll - analogs & derivatives
Chlorophyll - chemistry
Cofactors
Conformational analysis
Crystal structure
Derivatives
Mathematical analysis
Molecular Conformation
Molecular structure
Photosynthesis
Photosynthetic pigments
Photosynthetic Reaction Center Complex Proteins - chemistry
Physical Chemistry
Pigmentation
Pigments
Plant Sciences
Porphyrins - chemistry
Reaction centers
Solvents
Tetrapyrroles
Unit cell
Title Structure and conformation of photosynthetic pigments and related compounds. 15. Conformational analysis of chlorophyll derivatives - implications for hydroporphyrins in vivo
URI https://link.springer.com/article/10.1039/c8pp00500a
https://www.ncbi.nlm.nih.gov/pubmed/30964476
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https://www.proquest.com/docview/2206225280
Volume 18
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