2022
DOI: 10.1016/j.tetlet.2022.153760
|View full text |Cite
|
Sign up to set email alerts
|

Application of the advanced Marfey’s method for the determination of the absolute configuration of ogipeptins

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
9
0

Year Published

2022
2022
2024
2024

Publication Types

Select...
5

Relationship

2
3

Authors

Journals

citations
Cited by 5 publications
(9 citation statements)
references
References 12 publications
0
9
0
Order By: Relevance
“…To determine the absolute configurations of ogipeptins, we attempted to crystallize ogipeptins and their derivatives for X-ray structure analysis, but we were unable to acquire satisfactory X-ray diffraction data. In our previous work, we confirmed the existence of a 2:1 ratio of (2 S ,3 S ):(2 S ,3 R ) β-OH Dab isomers in ogipeptin A using the advanced Marfey’s method . Because ogipeptin A contains three consecutive β-OH Dabs, the order in which they are located can be confirmed only by performing the total synthesis of three diastereomers (Figure ) and comparing their analytical data to those of natural ogipeptin A.…”
mentioning
confidence: 64%
See 2 more Smart Citations
“…To determine the absolute configurations of ogipeptins, we attempted to crystallize ogipeptins and their derivatives for X-ray structure analysis, but we were unable to acquire satisfactory X-ray diffraction data. In our previous work, we confirmed the existence of a 2:1 ratio of (2 S ,3 S ):(2 S ,3 R ) β-OH Dab isomers in ogipeptin A using the advanced Marfey’s method . Because ogipeptin A contains three consecutive β-OH Dabs, the order in which they are located can be confirmed only by performing the total synthesis of three diastereomers (Figure ) and comparing their analytical data to those of natural ogipeptin A.…”
mentioning
confidence: 64%
“…In our previous work, we confirmed the existence of a 2:1 ratio of (2S,3S):(2S,3R) β-OH Dab isomers in ogipeptin A using the advanced Marfey's method. 11 ogipeptin A contains three consecutive β-OH Dabs, the order in which they are located can be confirmed only by performing the total synthesis of three diastereomers (Figure 1) and comparing their analytical data to those of natural ogipeptin A.…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…As a result, the unknown absolute configurations of the three residues of β-hydroxy-α,γdiaminobutyric acids (β-OH Dabs) composed of ogipeptins were elucidated. 10,11 By synthesizing these diastereomers, it is possible to confirm the significance of the existence of the secondary hydroxyl group of β-OH Dab. The modes of action of ogipeptins are not fully understood, but are assumed to be similar to those of polymyxins.…”
mentioning
confidence: 99%
“…As a result, the unknown absolute configurations of the three residues of the β-hydroxy-α,γ-diaminobutyric acids (β-OH Dabs) present in the ogipeptins were elucidated. 10 11 By synthesizing these diastereomers, it was possible to confirm the significance of the presence of the secondary hydroxy group in the β-OH Dabs.…”
mentioning
confidence: 99%