18 O/16 O-Encoding Strategy for Microscale Stereochemical Determination of Peptidic Natural Products.
Chem Asian J
; 16(17): 2447-2452, 2021 Sep 01.
Article
in En
| MEDLINE
| ID: mdl-34190394
ABSTRACT
The demand for more efficient methods of establishing the undetermined stereochemistries of peptidic natural products continues unabated. A new method for microscale stereochemical determination was devised by integrating solid-phase synthesis, split-and-mix randomization, 18 O/16 O-encoding of d/l-configurations, tandem mass spectrometry, and biological evaluation. Here we applied gramicidin A as the molecule for a blind test. Gramicidin A and its 31 diastereomers were randomly prepared in microgram scale with 18 O/16 O-stereochemical encoding and subjected to MS/MS-structural determination and cytotoxicity assay. Only the parent gramicidin A was selected from among the 32 stereoisomers, validating the high reliability of the present strategy.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Biological Products
/
Gramicidin
Type of study:
Clinical_trials
Language:
En
Journal:
Chem Asian J
Year:
2021
Document type:
Article
Affiliation country: