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Synthesis and biological evaluation of delavayin-C.

Shinde NV, Himaja M, Bhosale SK, Ramana MV, Sakarkar DM - Indian J Pharm Sci (2008)

Bottom Line: The synthesis of a cyclic heptapeptide, delavayin-C, cyclo(gly-tyr-tyr-tyr-pro-val-pro) is described.The structure of this compound was established on the basis of analytical IR, (1)H NMR and FAB mass spectral data.The antibacterial and antifungal activities of this peptide are also described.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, N. G. S. M. Institute of Pharmaceutical Sciences, Nanthoor, Mangalore-575 005, India.

ABSTRACT
The synthesis of a cyclic heptapeptide, delavayin-C, cyclo(gly-tyr-tyr-tyr-pro-val-pro) is described. The structure of this compound was established on the basis of analytical IR, (1)H NMR and FAB mass spectral data. The antibacterial and antifungal activities of this peptide are also described.

No MeSH data available.


Related in: MedlinePlus

Synthetic route for the synthesis of delavayin-C.a= DIPC, NMM, CHCl3, RT, 24 h, b= TFA, NMM, RT, 1 h, c= LiOH, THF:H2O (1:1), reflux, 15 mins, d= pnp-, CHCl3, RT, 12 h, e= NMM, CHCl3, 0°C, 7 d.
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Figure 0001: Synthetic route for the synthesis of delavayin-C.a= DIPC, NMM, CHCl3, RT, 24 h, b= TFA, NMM, RT, 1 h, c= LiOH, THF:H2O (1:1), reflux, 15 mins, d= pnp-, CHCl3, RT, 12 h, e= NMM, CHCl3, 0°C, 7 d.

Mentions: In order to carry out the total synthesis of cyclic peptide, cyclo(gly-tyr-tyr-tyr-pro-val-pro), it was disconnected into three dipeptide units, Boc-gly-tyr-OMe 1, Boc-tyr-tyr-OMe 2, Boc-pro-val-OMe 3 and a single amino acid methyl ester hydrochloride unit, pro-OMe-HCl 4. The required dipeptides were prepared by coupling Boc amino acids with the respective amino acid ester hydrochlorides using DIPC, CHCl3 and N-methyl morpholine according to Bondanszky8 procedure with suitable modifications. The Boc-group of the dipeptide 2 was removed by using trifluoroacetic acid and the ester group of dipeptide 1 was removed by using LiOH. The deprotected units were then coupled to get a tetrapeptide Boc-gly-tyr-tyr-tyr-OMe 5. Similarly, the dipeptide 3 was coupled with single amino acid methyl ester hydrochloride unit, pro-OMe HCl 4 after appropriate deprotection to get a tripeptide Boc-pro-val-pro-OMe 6. The resulting tetrapeptide and tripeptide was then coupled together by using DIPC, NMM and CHCl3 to get a linear heptapeptide Boc-gly-tyr-tyr-tyr-pro-val-pro-OMe 7. Finally cyclisation of this linear heptapeptide was carried out by p-nitrophenyl ester method. The intermediates and the final product were purified by recrystallisation from CHCl3. The retrosynthetic analysis of peptide is shown in the Scheme 1


Synthesis and biological evaluation of delavayin-C.

Shinde NV, Himaja M, Bhosale SK, Ramana MV, Sakarkar DM - Indian J Pharm Sci (2008)

Synthetic route for the synthesis of delavayin-C.a= DIPC, NMM, CHCl3, RT, 24 h, b= TFA, NMM, RT, 1 h, c= LiOH, THF:H2O (1:1), reflux, 15 mins, d= pnp-, CHCl3, RT, 12 h, e= NMM, CHCl3, 0°C, 7 d.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3040889&req=5

Figure 0001: Synthetic route for the synthesis of delavayin-C.a= DIPC, NMM, CHCl3, RT, 24 h, b= TFA, NMM, RT, 1 h, c= LiOH, THF:H2O (1:1), reflux, 15 mins, d= pnp-, CHCl3, RT, 12 h, e= NMM, CHCl3, 0°C, 7 d.
Mentions: In order to carry out the total synthesis of cyclic peptide, cyclo(gly-tyr-tyr-tyr-pro-val-pro), it was disconnected into three dipeptide units, Boc-gly-tyr-OMe 1, Boc-tyr-tyr-OMe 2, Boc-pro-val-OMe 3 and a single amino acid methyl ester hydrochloride unit, pro-OMe-HCl 4. The required dipeptides were prepared by coupling Boc amino acids with the respective amino acid ester hydrochlorides using DIPC, CHCl3 and N-methyl morpholine according to Bondanszky8 procedure with suitable modifications. The Boc-group of the dipeptide 2 was removed by using trifluoroacetic acid and the ester group of dipeptide 1 was removed by using LiOH. The deprotected units were then coupled to get a tetrapeptide Boc-gly-tyr-tyr-tyr-OMe 5. Similarly, the dipeptide 3 was coupled with single amino acid methyl ester hydrochloride unit, pro-OMe HCl 4 after appropriate deprotection to get a tripeptide Boc-pro-val-pro-OMe 6. The resulting tetrapeptide and tripeptide was then coupled together by using DIPC, NMM and CHCl3 to get a linear heptapeptide Boc-gly-tyr-tyr-tyr-pro-val-pro-OMe 7. Finally cyclisation of this linear heptapeptide was carried out by p-nitrophenyl ester method. The intermediates and the final product were purified by recrystallisation from CHCl3. The retrosynthetic analysis of peptide is shown in the Scheme 1

Bottom Line: The synthesis of a cyclic heptapeptide, delavayin-C, cyclo(gly-tyr-tyr-tyr-pro-val-pro) is described.The structure of this compound was established on the basis of analytical IR, (1)H NMR and FAB mass spectral data.The antibacterial and antifungal activities of this peptide are also described.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, N. G. S. M. Institute of Pharmaceutical Sciences, Nanthoor, Mangalore-575 005, India.

ABSTRACT
The synthesis of a cyclic heptapeptide, delavayin-C, cyclo(gly-tyr-tyr-tyr-pro-val-pro) is described. The structure of this compound was established on the basis of analytical IR, (1)H NMR and FAB mass spectral data. The antibacterial and antifungal activities of this peptide are also described.

No MeSH data available.


Related in: MedlinePlus