Synthesis of bile pigments. 9. Chemical total synthesis of (+)-(2R,16R)- and (+)-(2S,16R)-phycoerythrobilin dimethyl ester

Gossauer, Albert; Weller, Jens‐Peter

doi:10.1021/ja00486a053

Cited by 52 publications

(7 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The common difference between these two groups of bilins is the reduction state of the methine bridge between C15 and C16. CpeS bound bilins have a reduced 15,16 bond and thereby a new chiral center at C16 in the R configuration (49). In contrast, PCB-specific lyase-isomerase PecE/PecF from Mastigocladus laminosus binds only bilins with a 15,16 double bond (50).…”

Section: Discussionmentioning

confidence: 99%

CpeS Is a Lyase Specific for Attachment of 3Z-PEB to Cys82 of β-phycoerythrin from Prochlorococcus marinus MED4

Wiethaus

Busch

Kock

et al. 2010

Journal of Biological Chemistry

View full text Add to dashboard Cite

In contrast to the majority of cyanobacteria, the unicellular marine cyanobacterium Prochlorococcus marinus MED4 uses an intrinsic divinyl-chlorophyll-dependent light-harvesting system for photosynthesis. Despite the absence of phycobilisomes, this high-light adapted strain possesses ␤-phycoerythrin (CpeB), an S-type lyase (CpeS), and enzymes for the biosynthesis of phycoerythrobilin (PEB) and phycocyanobilin. Of all linear tetrapyrroles synthesized by Prochlorococcus including their 3Z-and 3E-isomers, CpeS binds both isomers of PEB and its biosynthetic precursor 15,16-dihydrobiliverdin (DHBV). However, dimerization of CpeS is independent of bilins, which are tightly bound in a complex at a ratio of 1:1. Although bilin binding by CpeS is fast, transfer to CpeB is rather slow. CpeS is able to attach 3E-PEB and 3Z-PEB to dimeric CpeB but not DHBV. CpeS transfer of 3Z-PEB exclusively yields correctly bound ␤Cys 82 -PEB, whereas ␤Cys 82 -DHBV is a side product of 3E-PEB transfer. Spontaneous 3E-and 3Z-PEB addition to CpeB is faulty, and products are in both cases ␤Cys 82 -DHBV and likely a PEB bound at ␤Cys 82 in a non-native configuration. Our data indicate that CpeS is specific for 3Z-PEB transfer to ␤Cys 82 of phycoerythrin and essential for the correct configuration of the attachment product.

show abstract

Section: Discussionmentioning

confidence: 99%

CpeS Is a Lyase Specific for Attachment of 3Z-PEB to Cys82 of β-phycoerythrin from Prochlorococcus marinus MED4

Wiethaus

Busch

Kock

et al. 2010

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…Fast atom bombardment mass spectra (FAB-MS) were measured in a ZAB-HS mass spectrometer; solid samples were dissolved in glycerol and then introduced to the instrument. The concentrations of biladienes were determined by calculation based on established molar extinction coefficients, log ePEBDM = 4.69 for PEBDM (Gossauer and Weller, 1978) and log eIBVDM = 4.10 for IBVDM (Stoll and Gray, 1970).…”

Section: Methodsmentioning

confidence: 99%

THE COMPLEXES FORMED BY BILADIENE a, b COMPOUNDS WITH ZINC IONS and THEIR APPLICATION IN DETERMINATION OF THE CHROMOPHORE COMPOSITION OF α‐ and β‐ SUBUNITS OF R‐PHYCOERYTHRIN

Cheng

Chiang

1990

Photochem & Photobiology

View full text Add to dashboard Cite

Abstract— –Phycoerythrobilin dimethyl ester (PEBDM) or isomesobiliviolin dimethyl ester (IBVDM) formed complexes with zinc ions in chloroform. The complex ratios were determined to be 1:1 according to the spectrophotometric titration of PEBDM and IBVDM with zinc ions in methanol and the mass spectra of the complexes. The chromophore compositions of R‐phycoerythrin from Porphyra yezoensis were determined by spectrophotometric titration of α‐ and β‐subunits at pH 13.0 with zinc ions. There were 2 phycoerythrobilins in the a‐subunit, and 1 phycourobilin and 3 phycoerythrobilins in the β‐subunit.

show abstract

“…The reaction of the monothioimide (7) (ring A) and the phosphorus ylide (8) (ring B), a general method for the synthesis of alkylidene lactams (GOSSAUER et al 1977), had been applied before to the synthesis of phycocyanobilin (GOSSAUER and HINZE 1978) and phycoerythrobilin WELLER 1978, GOSSAUER andKLAHR 1979). The introduction of the vinyl group starting from a primary hydroxyl function had also been applied to phycoerythrobilin (GOSSAUER and WELLER 1978). The final condensation reaction had also been applied before to a number of bile pigments.…”

Section: 4 Total Synthesismentioning

confidence: 99%

“…It has been assumed that the absolute configuration at C-2 which is R in phycoerythrobilin (GOSSAUER and WELLER 1978) and probably in phycocyanobilin (BROCKMANN and KNOBLOCH 1973) is also R in phytochromobilin, but direct evidence is still lacking (KLEIN et al 1977, LAGARIAS andRAPOPORT 1980). The assumption of the trans-configuration at ring A (i.e, 2R, 3R, or alternatively, 2S, 3S) was supported by the exclusive formation of trans-configurated products by addition of methanol or thiols to the ethylidene group of model imides and phycocyanobilin (KLEIN and RÜDIGER 1978.…”

mentioning

confidence: 99%

Chromophores in Photomorphogenesis

Rüdiger¹,

Scheer²

1983

Photomorphogenesis

View full text Add to dashboard Cite

Library of Congress Cataloging in PublicationThis work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks.Under §54 of the German Copyright Law where copies are made for other than private use, a fee is payable to "Verwertungsgesellschaft Wort" Munich. © by Springer-Verlag Berlin-Heidelberg 1983 Printed in GermanyThe use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use.Typesetting, printing and bookbinding: Universitätsdruckerei H. Stürtz AG, Würzburg.

show abstract

Synthesis of bile pigments. 9. Chemical total synthesis of (+)-(2R,16R)- and (+)-(2S,16R)-phycoerythrobilin dimethyl ester

Cited by 52 publications

References 18 publications

CpeS Is a Lyase Specific for Attachment of 3Z-PEB to Cys82 of β-phycoerythrin from Prochlorococcus marinus MED4

CpeS Is a Lyase Specific for Attachment of 3Z-PEB to Cys82 of β-phycoerythrin from Prochlorococcus marinus MED4

THE COMPLEXES FORMED BY BILADIENE a, b COMPOUNDS WITH ZINC IONS and THEIR APPLICATION IN DETERMINATION OF THE CHROMOPHORE COMPOSITION OF α‐ and β‐ SUBUNITS OF R‐PHYCOERYTHRIN

Chromophores in Photomorphogenesis

Contact Info

Product

Resources

About