Static and Dynamic Stereochemistry of Chiral Ln DOTA Analogues
Ln DOTA derivatives (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemica...
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| Published in | Chemphyschem Vol. 12; no. 8; pp. 1490 - 1497 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
06.06.2011
WILEY‐VCH Verlag |
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| Abstract | Ln DOTA derivatives (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemical description, with reference to conformational enthalpies. Yb is taken as the reference element because of its unique spectroscopic properties, namely, a small contact contribution to the paramagnetic shift and an intense near‐infrared electronic circular dichroism, endowed with an easily recognizable fine structure.
The introduction and control of defined chiral centers on the scaffold of DOTA (see structure) imparts rigidity to the system and increases its structural homogeneity. Different locations of these chiral elements lead to different degrees of conformational prevalence. |
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| AbstractList | Ln DOTA derivatives (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemical description, with reference to conformational enthalpies. Yb is taken as the reference element because of its unique spectroscopic properties, namely, a small contact contribution to the paramagnetic shift and an intense near‐infrared electronic circular dichroism, endowed with an easily recognizable fine structure. Ln DOTA derivatives (DOTA=1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemical description, with reference to conformational enthalpies. Yb is taken as the reference element because of its unique spectroscopic properties, namely, a small contact contribution to the paramagnetic shift and an intense near-infrared electronic circular dichroism, endowed with an easily recognizable fine structure.Ln DOTA derivatives (DOTA=1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemical description, with reference to conformational enthalpies. Yb is taken as the reference element because of its unique spectroscopic properties, namely, a small contact contribution to the paramagnetic shift and an intense near-infrared electronic circular dichroism, endowed with an easily recognizable fine structure. Ln DOTA derivatives (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which greatly modulate their chemical as well as their magnetic and optical properties. The subject is reviewed in terms of classical stereochemical description, with reference to conformational enthalpies. Yb is taken as the reference element because of its unique spectroscopic properties, namely, a small contact contribution to the paramagnetic shift and an intense near‐infrared electronic circular dichroism, endowed with an easily recognizable fine structure. The introduction and control of defined chiral centers on the scaffold of DOTA (see structure) imparts rigidity to the system and increases its structural homogeneity. Different locations of these chiral elements lead to different degrees of conformational prevalence. |
| Author | Salvadori, Piero Di Bari, Lorenzo |
| Author_xml | – sequence: 1 givenname: Lorenzo surname: Di Bari fullname: Di Bari, Lorenzo email: ldb@dcci.unipi.it organization: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, I-56126 Pisa (Italy), Fax: (+39) 50 2219 260 – sequence: 2 givenname: Piero surname: Salvadori fullname: Salvadori, Piero organization: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, I-56126 Pisa (Italy), Fax: (+39) 50 2219 260 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21547989$$D View this record in MEDLINE/PubMed |
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(e_1_2_10_16_2) 1994 e_1_2_10_19_2 e_1_2_10_1_2 e_1_2_10_3_2 e_1_2_10_17_2 e_1_2_10_52_2 e_1_2_10_5_2 e_1_2_10_15_2 e_1_2_10_38_2 e_1_2_10_54_2 e_1_2_10_7_2 e_1_2_10_13_2 e_1_2_10_36_2 e_1_2_10_56_2 e_1_2_10_9_2 e_1_2_10_12_2 e_1_2_10_33_2 e_1_2_10_10_2 e_1_2_10_31_2 e_1_2_10_50_2 e_1_2_10_28_2 e_1_2_10_26_2 e_1_2_10_49_2 e_1_2_10_24_2 e_1_2_10_47_2 e_1_2_10_45_3 |
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| Snippet | Ln DOTA derivatives (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which... Ln DOTA derivatives (DOTA=1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) are known to undergo relevant stereoisomeric equilibria in solution, which... |
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| SubjectTerms | chirality circular dichroism conformation lanthanides MRI contrast agents |
| Title | Static and Dynamic Stereochemistry of Chiral Ln DOTA Analogues |
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