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Total synthesis of the putative structure of the proposed Banyasin A.

Gao X, Ren Q, Choi S, Xu Z, Ye T - Front Chem (2015)

Bottom Line: The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described.The structure synthesized appears to be different from that of the natural product.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen, China.

ABSTRACT
The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described. The structure synthesized appears to be different from that of the natural product.

No MeSH data available.


Retrosynthetic analysis of banyasin A (1).
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Figure 3: Retrosynthetic analysis of banyasin A (1).

Mentions: The retrosynthetic analysis of banyasin A (1) is illustrated in Figure 3. The N-methyl carbamoyl modification of the Arg residue will be conducted as the final step of the synthesis. There are a number of possible positions to close the macrocyclic portion (2) of the molecule (Figure 2). We chose to close the cyclopeptide via macrolactamization between the alanine and amoa residues because it allowed versatility in the construction of the cyclization precursor (3). Because the absolute configuration of the 3-amino-2-methyl-5E-octenoic acid residue was not established, the incorporation of four possible diastereomers of the 3-amino-2-methyl-5E-octenoic acid residue to afford linear precursor 3 could be exerted in the late stage. Further disconnection of the linear peptide 3 revealed amoa unit (4) and a tetrapeptide equivalent, the latter intermediate being traced to the protected amino acids 5, 6, 7, and 8. (Figure 3).


Total synthesis of the putative structure of the proposed Banyasin A.

Gao X, Ren Q, Choi S, Xu Z, Ye T - Front Chem (2015)

Retrosynthetic analysis of banyasin A (1).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4362330&req=5

Figure 3: Retrosynthetic analysis of banyasin A (1).
Mentions: The retrosynthetic analysis of banyasin A (1) is illustrated in Figure 3. The N-methyl carbamoyl modification of the Arg residue will be conducted as the final step of the synthesis. There are a number of possible positions to close the macrocyclic portion (2) of the molecule (Figure 2). We chose to close the cyclopeptide via macrolactamization between the alanine and amoa residues because it allowed versatility in the construction of the cyclization precursor (3). Because the absolute configuration of the 3-amino-2-methyl-5E-octenoic acid residue was not established, the incorporation of four possible diastereomers of the 3-amino-2-methyl-5E-octenoic acid residue to afford linear precursor 3 could be exerted in the late stage. Further disconnection of the linear peptide 3 revealed amoa unit (4) and a tetrapeptide equivalent, the latter intermediate being traced to the protected amino acids 5, 6, 7, and 8. (Figure 3).

Bottom Line: The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described.The structure synthesized appears to be different from that of the natural product.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen, China.

ABSTRACT
The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described. The structure synthesized appears to be different from that of the natural product.

No MeSH data available.