A fast and simplein situ method for the determination of the absolute configuration of amino acid esters using the chiroptical properties of their Eu(FOD)3 complexes

Amino Acids ◽  
1992 ◽  
Vol 3 (2) ◽  
pp. 195-203 ◽  
Author(s):  
V. Toome ◽  
B. Wegrzynski
Keyword(s):  
Amino Acid ◽  
Absolute Configuration ◽  
Amino Acid Esters ◽  
Chiroptical Properties ◽  
The Absolute ◽  
Acid Esters

Determination of the Relative Configuration of β-Amino Acid Esters Based on Residual Dipolar Couplings

2015 ◽  
Vol 2015 (31) ◽  
pp. 6801-6805 ◽  
Author(s):  
Thomas Niklas ◽  
Christian Steinmetzger ◽  
Weiping Liu ◽  
Daniel Zell ◽  
Dietmar Stalke ◽  
...  
Keyword(s):  
Amino Acid ◽  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Amino Acid Esters ◽  
Relative Configuration ◽  
Acid Esters

scholarly journals Absolute Stereochemistry of the β-Hydroxy Acid Unit in Hantupeptins and Trungapeptins

2016 ◽  
Vol 11 (1) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Deepak Kumar Gupta ◽  
Gary Chi Ying Ding ◽  
Yong Chua Teo ◽  
Lik Tong Tan
Keyword(s):  
Amino Acid ◽  
Structural Feature ◽  
Absolute Configuration ◽  
Hydroxy Acid ◽  
Hplc Analysis ◽  
The Absolute ◽  
Absolute Stereochemistry ◽  
Common Structural Feature ◽  
Acid Unit

The β-hydroxy/amino acid unit is a common structural feature of many bioactive marine cyanobacterial depsipeptides. In this study, the absolute stereochemistry of the β-hydroxy acid moieties in hantupeptins and trungapeptins were determined through their synthesis and HPLC analysis of the Mosher ester derivatives. Synthesis of two3-hydroxy-2-methyloctanoic acid (Hmoa) stereoisomers, (2 S,3 R)-Hmoa and (2 S,3 S)-Hmoa, were achieved using diastereoselective asymmetric method and the retention times of all four Hmoa isomers were established indirectly by RPLC-MS analysis of their Mosher ester derivative standards. Based on the retention times of the standards, the absolute configuration of the Hmoa unit in hantupeptin C (3) and trungapeptin C (6) was assigned as (2 R,3 S)- and (2 S,3 R)-Hmoa, respectively. The use of the Mosher's reagents, coupled with HPLC analysis, provided a viable alternative to the absolute stereochemical determination of β-hydroxy acid units in depsipeptides.

Chiroptical properties of amino acid esters

Tetrahedron ◽  
1980 ◽  
Vol 36 (13) ◽  
pp. 2019-2020 ◽  
Author(s):  
O. Korver ◽  
Th.J. Liefkens
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Chiroptical Properties ◽  
Acid Esters

ChemInform Abstract: A New 31P NMR Method for the Enantiomeric Excess Determination of Alcohols, Amines, and Amino Acid Esters.

ChemInform ◽  
2010 ◽  
Vol 24 (28) ◽  
pp. no-no
Author(s):  
R. HULST ◽  
R. W. J. ZIJLSTRA ◽  
B. L. FERINGA ◽  
N. KOEN DE VRIES ◽  
W. TEN HOEVE ◽  
...  
Keyword(s):  
Amino Acid ◽  
31P Nmr ◽  
Enantiomeric Excess ◽  
Amino Acid Esters ◽  
Nmr Method ◽  
Acid Esters

CD exciton chirality method for determination of the absolute configuration of ?-hydroxy-?-amino acid derivatives

Chirality ◽  
2001 ◽  
Vol 13 (5) ◽  
pp. 266-271 ◽  
Author(s):  
Lee-Chiang Lo ◽  
Jean-Yin Chen ◽  
Chun-Tzu Yang ◽  
Der-Shang Gu
Keyword(s):  
Amino Acid ◽  
Absolute Configuration ◽  
Amino Acid Derivatives ◽  
Hydroxy Amino Acid ◽  
Hydroxy Amino ◽  
The Absolute
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