| Project/Area Number |
06640702
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Organic chemistry
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| Research Institution | Toho University |
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Principal Investigator |
TAMAKI Makoto Toho Univ, Chemisrty, Associate professor, 理学部, 助教授 (00104141)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1995: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1994: ¥1,700,000 (Direct Cost: ¥1,700,000)
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| Keywords | Gramicidin S / Direct synthesis / Cyclic dimerization / No protecting group / グラミジシンS |
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| Research Abstract |
To investigare the formation mechanism of gramicidin S (GS) by the dimerization-cyclization of pentapeptide active eaters having no protecting group on the side chain of the Orn residue, the cyclization of four H-X-Pro-Y-Orn-Leu-ONSu's (X=L- or D-Phe, Y=L- or D-Val, -ONSu=succinimide ester) was examined. Only H-D-Phe-Pro-Val-Orn-Leu-ONSu gave semi-GS (cyclic monomer) and GS (cyclic dimer).
1. H-D-Phe-Pro-Val-Orn-Leu-ONSu
2. H-Phe-Pro-D-Val-Orn-Leu-ONSu
3. H-Phe-Pro-Val-Orn-Leu-ONSu
4. H-D-Phe-Pro-D-Val-Orn-Leu-ONSu
The active ester with D-Phe-Pro-D-Val sequence produced exclusively [D-Val] -semi-GS in 58% yield. On the other hand, the active esters having Phe-Pro-Val and Phe-Pro-D-Val sequences did not yield any amount of cyclic monomer and cyclic dimer. A good correlation among the CD spectra in ethanol, NMR spectra in DMSO-d_6 of the pentapeptide ethyl esters, and the cyclization of the active esters was found.
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