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

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.

scholarly journals Studies on Hydroxy Amino Acids. IV. Syntheses of Several Peptides Containing Aziridinecarboxylic Acid Derived from the Corresponding Hydroxy Amino Acid Derivatives

1972 ◽  
Vol 45 (4) ◽  
pp. 1162-1167 ◽  
Author(s):  
Yasuo Nakagawa ◽  
Takashi Tsuno ◽  
Kiichiro Nakajima ◽  
Michio Iwai ◽  
Haruki Kawai ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Hydroxy Amino Acid ◽  
Hydroxy Amino

Determination of the Complete Absolute Configuration of Petriellin A

2006 ◽  
Vol 59 (6) ◽  
pp. 407 ◽  
Author(s):  
Luigi Aurelio ◽  
Robert T. C. Brownlee ◽  
Jason Dang ◽  
Andrew B. Hughes ◽  
Gideon M. Polya
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Natural Product ◽  
Absolute Configuration ◽  
Structural Determination ◽  
Amino Acid Residues ◽  
The Common ◽  
The Absolute ◽  
Derivatives Of

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey’s derivatives and Marfey’s derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.

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