Abstract
Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.
| Original language | English |
|---|---|
| Pages (from-to) | 340-346 |
| Number of pages | 7 |
| Journal | Chirality |
| Volume | 14 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2002 |
| Externally published | Yes |
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Keywords
- Chiral discrimination
- Chiral separation
- Circular dichroic spectroscopy (CD)
- Cyclopropyl retinoid
- Exciton coupled CD
- Rhodopsin
ASJC Scopus subject areas
- Analytical Chemistry
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin. / Fujimoto, Yukari; Xie, Rongyuan; Tully, Sarah E.; Berova, Nina; Nakanishi, Koji.
In: Chirality, Vol. 14, No. 4, 2002, p. 340-346.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin
AU - Fujimoto, Yukari
AU - Xie, Rongyuan
AU - Tully, Sarah E.
AU - Berova, Nina
AU - Nakanishi, Koji
PY - 2002
Y1 - 2002
N2 - Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.
AB - Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.
KW - Chiral discrimination
KW - Chiral separation
KW - Circular dichroic spectroscopy (CD)
KW - Cyclopropyl retinoid
KW - Exciton coupled CD
KW - Rhodopsin
UR - http://www.scopus.com/inward/record.url?scp=0036230852&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036230852&partnerID=8YFLogxK
U2 - 10.1002/chir.10076
DO - 10.1002/chir.10076
M3 - Article
C2 - 11968076
AN - SCOPUS:0036230852
VL - 14
SP - 340
EP - 346
JO - Chirality
JF - Chirality
SN - 0899-0042
IS - 4
ER -