• Bulletin of the Korean Chemical Society
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• v.28 no.12
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• pp.2414-2418
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• 2007

N-Hydroxy diketopiperazine derivatives from L- and D-forms of Ser and Cys were synthesized for the first time and the ring conformation of both analogues in water was determined to be close to flat via NMR and ab initio calculations. However, the side chain of the Ser analogue was oriented toward a pseudo-equatorial position while that of the Cys analogue was slightly oriented toward a pseudo-axial direction, with a slightly distorted boat-shaped ring conformation. Among them, the D-Cys analogue was found to be a weak inhibitor of α- glucosidase.

• Korean Journal of Pharmacognosy
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• v.44 no.4
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• pp.336-343
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• 2013

In a continuation of investigation on Cordyceps militaris, thirteen compounds were isolated from the $CH_2Cl_2$ and n-BuOH-soluble fraction of C. militaris. They were identified as twelve diketopiperazines such as cyclo($\small{L}$-Gly-$\small{L}$-Pro) (1), cyclo($\small{L}$-Ala-$\small{L}$-Pro) (2), cyclo($\small{L}$-Ser-$\small{L}$-Pro) (3), cyclo($\small{L}$-Val-$\small{L}$-Pro) (4), cyclo($\small{L}$-Thr-$\small{L}$-Pro) (5), cyclo($\small{L}$-Pro-$\small{L}$-Pro) (6), cyclo($\small{L}$-Thr-$\small{L}$-Leu) (7), cyclo($\small{L}$-Tyr-$\small{L}$-Ala) (8), cyclo($\small{L}$-Phe-$\small{L}$-Ser) (9), cyclo($\small{L}$-Phe-$\small{L}$-Pro) (10), cyclo($\small{L}$-Tyr-$\small{L}$-Pro) (11) and brevianamide F (13), and an amino acid, tryptophan (12). Their structures were identified on the basis of chemical evidences and spectroscopic analysis including 1D-NMR ($^1H$, $^{13}C$), 2D-NMR (HSQC, HMBC) and MS spectral data. Among the isolated compounds, compounds 1, 2, 6-11 are first reported from C. militaris.

• Journal of the Korean Chemical Society
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• v.26 no.5
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• pp.296-303
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• 1982

The solubilities of 1-phenyl-2-acetamido-3-butanone were measured in $H_2O$ at 20, 30 and 40$^{\circ}$C at pressure from 1 to 4500 kg/$cm^2$. Pressure going up to 4500 kg/$cm^2$, the solubility in $H_2O$decreases consistantly as that of diketopiperazine does. As diketopiperazine is a model compound of peptide bond and 1-phenyl-2-acetamido-3-butanone has only one peptide bond and a pretty large hydrophobic group, the solubility behavior is quite surprising. Volume change and heat capacity change data are reasonable.

• Journal of the Korean Chemical Society
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• v.59 no.6
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• pp.545-550
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• 2015

• Proceedings of the Korean Society of Fisheries Technology Conference
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• 2002.10a
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• pp.175-176
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• 2002

Rice blast, caused by Pyricularia oryzae (P. oryzae), is generally considered to be the most serious fungal disease of rice by its widespread distribution and destructiveness (Manandhar et al., 1998). The pathogenic fungus directly penetrates into the rice plant from a cellular structure called an appressorium that is formed at the tip of the germ tube. And the fungus can attack any aerial part of the rice plant, including seeds, in which the fungus may overwinter for several years. (omitted)

• Bulletin of the Korean Chemical Society
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• v.34 no.10
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• pp.3109-3112
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• 2013

• Korean Journal of Microbiology
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• v.52 no.4
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• pp.415-420
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• 2016

Chemical study of an Arctic bacterium, Pseudomonas aeruginosa (Pseudomonadaceae) led to the isolation of two diketopiperazines 1 and 2, two phenazine alkaloids 3 and 4, and an indole carbaldehyde 5, along with a benzoic acid derivative 6. The structures of the compounds were confirmed by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with published values. Among the isolates, compounds 5 and 6 were isolated for the first time from P. aeruginosa of the seawater of Arctic Chuckchi Sea. Antimicrobial activities of compounds 1‒6 against a Staphylococcus aureus and Candida albicans were evaluated.

• Analytical Science and Technology
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• v.6 no.1
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• pp.39-45
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• 1993

We have examined Raman spectra of cis-peptide model complex, diketopiperazine in water and $D_2O$ with 320 nm through 218 nm excitation. Our study examines assignment of the resonance enhanced amide vibrations and characterizes their enhancement mechanism. Three resonance enhaned cis-peptide marker bands were observed in aqueous solution at 1676, 1533 and $806cm^{-1}$, which were assigned to the cis-amide I, II and S band, respectively. The $1533cm^{-1}$ amide II band, which is almost pure C-N stretching, was most dominant in water and shifted to $1520cm^{-1}$ upon N-deuteration. This band will be probably a potential probe band for cis-peptide moieties in proteins. The excitation profile data and an Albrecht A-term fit indicated that the cis-peptide vibrations derive their intensities from the 188 nm cis-peptide ${\pi}-{\pi}^*$ electronic transition. We Propose that the geometry of cis-peptide ${\pi}^*$ excited state is C-N bond displacement relative to that of electronic ground state.

• Natural Product Sciences
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• v.13 no.3
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• pp.251-254
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• 2007

Dioxopiperazine alkaloids, 12R,13S-dihydroxyfumitremorgin C (1), fumitremorgin C (2), and brevianamide F (3), were isolated from the marine-derived fungus Pseudallescheria, and the absolute stereostructures of compounds 1 - 3 were elucidated on the basis of chemical and physicochemical evidence. Compounds 1 - 3 showed an antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The MIC (minimum inhibitory concentration) values of compounds 1 - 3 were 125 ${\mu}g/mL$ for all strains.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1997.11a
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• pp.19-25
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• 1997

Bicyclomycin(BCM)은 1972년에 일본 Hokkaido, Sapporo지방의 토양균중의 하나인 Streptomyces Sapporoneosis의 배양액으로부터 최초로 분리된 항생물질로서 특히 Gram(-) 박테리아인 Escherichia coli. Klebsiella, Shigella, Salmonella, Citrobacter, Enterobacter cloacae, Neisseria gonorrhoeae등에 대한 선택적인 항균효과를 가지고 있고 Streptomycin, Kanamycin, Chloramphenicol, Tetracyclin, Aminobenzylpenicillin 및 naldixic acid 등에 대해 교차내성을 가지고 있지 않다. BCM은 구조적인 면에서 [4.2.2]bicyclic구조를 가지고있는 특이한 항생물질로서 C(1)-triol부분, diketopiperazine부분 그리고 C(5)-C(5a)exomethylene의 3 부분으로 크게 나눌수 있다(Fig. 1). BGM은 E. coli에 대한 항균력으로서 250-500 $\mu\textrm{g}$/mL의 MIC value를 가지고 있고 급성독성으로서 LD$_{50}$가 4g/kg 이상으로 거의 독성이 없는 것이 특징이다. 현재 Fujisawa pharmaceutical Ltd.로부터 Bicozamycin이라는 상품명으로 설사치료제 용도로 시판되고 있다.