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Journal articles on the topic 'Cyclo(Phe-Pro)'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

Li, Dan-dan, Ying Wang, Eun La Kim, Jongki Hong, and Jee H. Jung. "Neuroprotective Effect of Cyclo-(L-Pro-L-Phe) Isolated from the Jellyfish-Derived Fungus Aspergillus flavus." Marine Drugs 19, no. 8 (2021): 417. http://dx.doi.org/10.3390/md19080417.

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Peroxisome proliferator-activated receptor (PPAR) expression has been implicated in pathological states such as cancer, inflammation, diabetes, and neurodegeneration. We isolated natural PPAR agonists—eight 2,5-diketopiperazines—from the jellyfish-derived fungus Aspergillus flavus. Cyclo-(L-Pro-L-Phe) was the most potent PPAR-γ activator among the eight 2,5-DKPs identified. Cyclo-(L-Pro-L-Phe) activated PPAR-γ in Ac2F rat liver cells and SH-SY5Y human neuroblastoma cells. The neuroprotective effect of this partial PPAR-γ agonist was examined using the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl

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2

Bina, Xiaowen R., and James E. Bina. "The Cyclic Dipeptide Cyclo(Phe-Pro) Inhibits Cholera Toxin and Toxin-Coregulated Pilus Production in O1 El Tor Vibrio cholerae." Journal of Bacteriology 192, no. 14 (2010): 3829–32. http://dx.doi.org/10.1128/jb.00191-10.

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ABSTRACT Cyclo(Phe-Pro) is a cyclic dipeptide produced by multiple Vibrio species. In this work, we present evidence that cyclo(Phe-Pro) inhibits the production of the virulence factors cholera toxin (CT) and toxin-coregulated pilus (TCP) in O1 El Tor Vibrio cholerae strain N16961 during growth under virulence gene-inducing conditions. The cyclo(Phe-Pro) inhibition of CT and TCP production correlated with reduced transcription of the virulence regulator tcpPH and was alleviated by overexpression of tcpPH.

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3

Lozano-González, M., B. Ovalle-Magallanes, M. Rangel-Grimaldo, et al. "Antidiabeticin vitroandin vivoevaluation of cyclodipeptides isolated fromPseudomonas fluorescensIB-MR-66e." New Journal of Chemistry 43, no. 20 (2019): 7756–62. http://dx.doi.org/10.1039/c9nj00645a.

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4

Yang, Xueqiong, Yabin Yang, Tianfeng Peng, et al. "A New Cyclopeptide from Endophytic Streptomyces sp. YIM 64018." Natural Product Communications 8, no. 12 (2013): 1934578X1300801. http://dx.doi.org/10.1177/1934578x1300801225.

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One new cyclopeptide, cyclo(L-Phe-L-Ala-L-Phe-Gly), named as vinaceuline (1) and three known cyclodipeptides, cyclo (Phe-Gly), cyclo (Phe-4-hydroxyl-Pro) and cyclo (Phe-Ile) were isolated from broth culture of endophytic Streptomyces YIM 64018 associated with Paraboea sinensis. The planar structure of the new compound was assigned on the basis of 1D and 2D NMR spectroscopic techniques, while the absolute configurations of the amino acid residues were determined by application of the advanced Marfey method. Cyclotetrapeptides are rarely found as Streptomycete metabolites.

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5

Sun, Shu-Jing, Yun-Chao Liu, Cai-Hong Weng, et al. "Cyclic Dipeptides Mediating Quorum Sensing and Their Biological Effects in Hypsizygus Marmoreus." Biomolecules 10, no. 2 (2020): 298. http://dx.doi.org/10.3390/biom10020298.

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A novel quorum sensing (QS) system was discovered in Serratia odorifera, the symbiotic bacterium of Hypsizygus marmoreus. This system uses cyclo(Pro-Phe), cyclo(Pro-Tyr), cyclo(Pro-Val), cyclo(Pro-Leu), cyclo(Tyr-Leu), and cyclo(Tyr-Ile) as autoinducers. This discovery is the first attempt to characterize cyclic dipeptides as QS signaling molecules in S. odorifera and improves the classical QS theory. Significantly, except for cyclo(Tyr-Leu), these QS autoinducers can increase the transcription level of lignin-degrading enzyme genes of H. marmoreus. The cyclo(Pro-Phe) can increase the activity

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6

Brice-Tutt, Ariana C., Sanjeewa N. Senadheera, Michelle L. Ganno, et al. "Phenylalanine Stereoisomers of CJ-15,208 and [d-Trp]CJ-15,208 Exhibit Distinctly Different Opioid Activity Profiles." Molecules 25, no. 17 (2020): 3999. http://dx.doi.org/10.3390/molecules25173999.

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The macrocyclic tetrapeptide cyclo[Phe-d-Pro-Phe-Trp] (CJ-15,208) and its stereoisomer cyclo[Phe-d-Pro-Phe-d-Trp] exhibit different opioid activity profiles in vivo. The present study evaluated the influence of the Phe residues’ stereochemistry on the peptides’ opioid activity. Five stereoisomers were synthesized by a combination of solid-phase peptide synthesis and cyclization in solution. The analogs were evaluated in vitro for opioid receptor affinity in radioligand competition binding assays, and for opioid activity and selectivity in vivo in the mouse 55 °C warm-water tail-withdrawal assa

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7

Ström, Katrin, Jörgen Sjögren, Anders Broberg, and Johan Schnürer. "Lactobacillus plantarum MiLAB 393 Produces the Antifungal Cyclic Dipeptides Cyclo(l-Phe-l-Pro) and Cyclo(l-Phe-trans-4-OH-l-Pro) and 3-Phenyllactic Acid." Applied and Environmental Microbiology 68, no. 9 (2002): 4322–27. http://dx.doi.org/10.1128/aem.68.9.4322-4327.2002.

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ABSTRACT We have isolated a Lactobacillus plantarum strain (MiLAB 393) from grass silage that produces broad-spectrum antifungal compounds, active against food- and feed-borne filamentous fungi and yeasts in a dual-culture agar plate assay. Fusarium sporotrichioides and Aspergillus fumigatus were the most sensitive among the molds, and Kluyveromyces marxianus was the most sensitive yeast species. No inhibitory activity could be detected against the mold Penicillium roqueforti or the yeast Zygosaccharomyces bailii. An isolation procedure, employing a microtiter well spore germination bioassay,

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8

Budesinsky, Milos, Ivana Cisarova, Frans Borremans, Jose C. Martins, and Ewald Pauwels. "Solid-state structure of cyclic dipeptides: an X-ray and computational study of cis- and trans-diketopiperazines of N-methyl-phenylalanine with the thia-pipecolic acids and thia-prolines." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 73, no. 6 (2017): 1179–93. http://dx.doi.org/10.1107/s2052520617014731.

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Ten new crystal structures of cis and trans bicyclic diketopiperazines (DKPs) of thia-pipecolic acid (with sulfur in the β, γ or δ position) or thia-proline (with sulfur in the β or γ position) and N-methyl phenylalanine [(NMe)Phe]: cyclo[(β-S)Pip-(NMe)Phe], cyclo[(γ-S)Pip-(NMe)Phe], cyclo[(δ-S)Pip-(NMe)Phe], cyclo[(β-S)Pro-(NMe)Phe] and cyclo[(γ-S)Pro-(NMe)Phe] were determined with X-ray crystallography. Density functional theory calculations of these molecules in the gas phase succeed in reproducing the observed molecular conformations in the crystal remarkably well. This illustrates the wea

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9

Kessler, Horst, and Arndt Müller. "Peptidkonformationen, 41. Eine ungewöhnliche Konformation des cyclischen Pentapeptids cyclo(-Pro-Pro-Phe-Phe-Gly-) in DMSO." Liebigs Annalen der Chemie 1986, no. 10 (1986): 1687–704. http://dx.doi.org/10.1002/jlac.198619861003.

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10

Rajesh, B. M., Javed Iqbal, N. Jagadeesh Babu, and Ashwini Nangia. "Water mediated tube in tetrapeptide cyclo(Phe-Pro-Leu-Aha) trihydrate and crystal structure of cyclo(d-Phe-Pro-Leu-Aha) anhydrate." CrystEngComm 9, no. 10 (2007): 860. http://dx.doi.org/10.1039/b709700j.

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11

Shaala, Lamiaa A., Diaa T. A. Youssef, Jihan M. Badr, Steve M. Harakeh, and Grégory Genta-Jouve. "Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived Streptomyces Species." Marine Drugs 17, no. 10 (2019): 584. http://dx.doi.org/10.3390/md17100584.

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Fractionation and purification of the ethyl acetate extract of the culture of a sponge-derived actinomycete, Streptomyces species Call-36, resulted in the isolation and identification of a new diketopiperazine, actinozine A (1), cyclo(2-OH-d-Pro-l-Leu) (2), two new nucleosides, thymidine-3-mercaptocarbamic acid (3) and thymidine-3-thioamine (4), together with cyclo(d-Pro-l-Phe) (5) and cyclo(l-Pro-l-Phe) (6). The structure assignments of the compounds were carried out by interpretation of 1D and 2D NMR data and mass spectral determinations. The absolute configurations of 1 and 2 were determine

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12

Liao, Shengrong, Ying Xu, Yong Tang, et al. "Design, synthesis and biological evaluation of soluble 2,5-diketopiperazines derivatives as potential antifouling agents." RSC Advances 5, no. 63 (2015): 51020–26. http://dx.doi.org/10.1039/c5ra06210a.

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13

Perzborn, Mareike, Christoph Syldatk, and Jens Rudat. "Separation of Cyclic Dipeptides (Diketopiperazines) from Their Corresponding Linear Dipeptides by RP-HPLC and Method Validation." Chromatography Research International 2013 (February 14, 2013): 1–8. http://dx.doi.org/10.1155/2013/310269.

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Simple, rapid, sensitive, precise, and accurate methods for detection and separation of seven diketopiperazines (DKPs), cyclo(Gly-Gly), cyclo(dl-Ala-dl-Ala), cyclo(l-Asp-l-Phe), cyclo(l-Asp-l-Asp), cyclo(Gly-l-Phe), cyclo(l-Pro-l-Tyr), and cyclo(l-Arg-l-Arg), from their corresponding linear dipeptides and related amino acids l-Phe and l-Tyr by reversed-phase high-performance liquid chromatography (RP-HPLC) were established. Moreover, for the racemic DKP cyclo(dl-Ala-dl-Ala) and dipeptide dl-Ala-dl-Ala, separation of the diastereomers was achieved. All methods can be performed within 15 min. Fo

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14

Long, Cong, Xiao-Ling Lu, Yun Gao, Bing-Hua Jiao, and Xiao-Yu Liu. "Description of aSulfitobacterStrain and Its Extracellular Cyclodipeptides." Evidence-Based Complementary and Alternative Medicine 2011 (2011): 1–6. http://dx.doi.org/10.1155/2011/393752.

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A marine bacterium M44 was separated from 30 m deep seawater in the East China Sea (26° 28.3′ N 122° 29.0′ E) in 2006. 16S rDNA gene sequence comparison showed that the strain M44 was a member of the genusSulfitobacterand highly similar to KMM 3554T. A series of experiments demonstrated that this strain M44 had many distinctive characteristics: its cells were gram-negative and mesophilic; its colonies were slightly yellowish, round, convex, and smooth; and it could grow at 10–28°C, pH 6.0–10.0, and in the presence of 0–12.5% (w/v) NaCl; the optimum growth conditions were 25°C and pH 7.0, and t

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15

Iwasaki, Yu, Yuki Taga, Asahi Suzuki, Mihoko Kurokawa, Yoshio Sato, and Yasutaka Shigemura. "Effect of Co-Ingestion of Collagen Peptides with Yogurt on Blood Absorption of Short Chain Hydroxyproline Peptides." Applied Sciences 10, no. 12 (2020): 4066. http://dx.doi.org/10.3390/app10124066.

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Collagen peptides (CP) have been used as functional foods for enhancing skin and joint health. Further degradation of CP results in peptide sizes small enough to enter the bloodstream following absorption in the small intestine. We examined the effects of food matrices on CP degradation into short chain peptides and absorption efficiency after ingestion. Changes to hydroxyproline (Hyp)-containing peptide levels in CP after yogurt fermentation and in human plasma by co-ingestion of CP and yogurt, with or without fermentation, were evaluated by liquid chromatography-mass spectrometry (LC-MS). Th

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16

Luo, Guangyuan, Jiajia Lang, Zhigang She, et al. "Nitrogen-Containing Compounds From Mangrove-Derived Fungus Aspergillus sp. 87." Natural Product Communications 15, no. 4 (2020): 1934578X2091531. http://dx.doi.org/10.1177/1934578x20915314.

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Nine nitrogen-containing compounds including 1 new alkaloid, aspergilamide A (1), and 8 known alkaloids and dipeptides, pseurotin A (2), fumigaclavine C (3), isochaetominine (4), cyclo(L-Pro-L-tyr) (5), cyclo- trans-4-OH-(L)-Pro-(L)-Phe (6), brevianamide F (7), and spirotryprostatins A and B (8 and 9), were obtained from the mangrove-derived fungus Aspergillus sp. 87. Their structures were identified by extensive spectroscopic analyses. All compounds did not show significant antibacterial activities.

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17

Bach, Alvin C., and Lila M. Gierasch. "Dehydrophenylalanine as the i + 2th residue of a .beta. turn: synthesis and conformational analysis of cyclo(Gly-Pro-.DELTA.z-Phe-D-Ala-Pro) and cyclo(Gly-Pro-D-Phe-D-Ala-Pro)." Journal of the American Chemical Society 107, no. 11 (1985): 3349–50. http://dx.doi.org/10.1021/ja00297a052.

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18

Park, Dae-Kyun, Ko-Eun Lee, Chang-Ho Baek, et al. "Cyclo(Phe-Pro) Modulates the Expression of ompU in Vibrio spp." Journal of Bacteriology 188, no. 6 (2006): 2214–21. http://dx.doi.org/10.1128/jb.188.6.2214-2221.2006.

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ABSTRACT Vibrio vulnificus was found to produce a chemical that induced the expression of Vibrio fischeri lux genes. Electron spray ionization-mass spectrometry and 1H nuclear magnetic resonance analyses indicated that the compound was cyclo(l-Phe-l-Pro) (cFP). The compound was produced at a maximal level when cell cultures reached the onset of stationary phase. Sodium dodecyl sulfate-polyacrylamide gel analysis of the total proteins of V. vulnificus indicated that expression of OmpU was enhanced by exogenously added synthetic or purified cFP. A toxR-null mutant failed to express ompU despite

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19

Saviano, Gabriella, Filomena Rossi, Ettore Benedetti, et al. "ChemInform Abstract: Structural Consequences of Metal Complexation of cyclo[Pro-Phe-Phe-Ala-Xaa]2 Decapeptides." ChemInform 33, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.200205187.

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20

ZANOTTI, GIANCARLO, MICHELE SAVIANO, GABRIELLA SAVIANO, et al. "Structure of cyclic peptides: the crystal and solution conformation of cyclo(Phe-Phe-Aib-Leu-Pro)." Journal of Peptide Research 51, no. 6 (2009): 460–66. http://dx.doi.org/10.1111/j.1399-3011.1998.tb00645.x.

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21

OZEKI, EIICHI, SHUNSAKU KIMURA, and YUKIO IMANISHI. "Conformation and complexation with metal ions of cyclic hexapeptides: cyclo (l-Leu-l-Phe-l-Pro)2 and cyclo (l-Cys(Acm)-l-Phe-l-Pro]2." International Journal of Peptide and Protein Research 34, no. 2 (2009): 111–17. http://dx.doi.org/10.1111/j.1399-3011.1989.tb01498.x.

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22

Carrieri, Raffaele, Giorgia Borriello, Giulio Piccirillo, et al. "Antibiotic Activity of a Paraphaeosphaeria sporulosa-Produced Diketopiperazine against Salmonella enterica." Journal of Fungi 6, no. 2 (2020): 83. http://dx.doi.org/10.3390/jof6020083.

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A diketopiperazine has been purified from a culture filtrate of the endophytic fungus Paraphaeosphaeria sporulosa, isolated from healthy tissues of strawberry plants in a survey of microbes as sources of anti-bacterial metabolites. Its structure has been determined by nuclear magnetic resonance (NMR) and liquid chromatography–mass spectrometry (LC–MS) analyses and was found to be identical to cyclo(L-Pro-L-Phe) purified from species of other fungal genera. This secondary metabolite has been selected following bioguided-assay fractionation against two strains of Salmonella enterica, the causal

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23

Yang, Wenzhi, Guangjie Liang, Yang Sun, and Zhijin Gong. "Bioactive Secondary Metabolites from Marine Streptomyces griseorubens f8: Isolation, Identification and Biological Activity Assay." Journal of Marine Science and Engineering 9, no. 9 (2021): 978. http://dx.doi.org/10.3390/jmse9090978.

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Marine actinomycetes are a potential source of a wide variety of bioactive natural products. Herein, four cyclic dipeptides, namely, cyclo(L-Val-L-Pro) (compound 1), cyclo(L-Pro-L-Leu) (compound 2), cyclo(L-Pro-L-Tyr) (compound 3) and cyclo(L-Pro-L-Phe) (compound 5), and an N-acetyltyramine (compound 4) were first isolated and identified as products of the marine Streptomyces griseorubens f8. Compounds 3 and 5 exhibit antibacterial activity against Staphylococcus aureus, Klebsiella aerogenes and Proteus vulgaris. The minimum inhibitory concentrations (MICs) against Staphylococcus aureus, Klebs

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24

ISHIZU, Takashi, Jungo HIRAYAMA, and Shunsaku NOGUCHI. "Complex Formation of Cyclo(L-Phe-L-Pro)4 with Noradrenaline Hydrochloride." CHEMICAL & PHARMACEUTICAL BULLETIN 42, no. 5 (1994): 1146–48. http://dx.doi.org/10.1248/cpb.42.1146.

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25

Inoue, Shoichiro, Jun Takanari, Keima Abe, Ayako Nagayama, Yukinobu Ikeya, and Noriyuki Kohda. "Isolation and Structure Determination of a Heat Shock Protein Inducer, Asparagus-Derived Proline-Containing 3-Alkyldiketopiperazines (Asparaprolines), From a Standardized Extract of Asparagus officinalis Stem." Natural Product Communications 15, no. 3 (2020): 1934578X2091468. http://dx.doi.org/10.1177/1934578x20914681.

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ETAS® has been developed from the stems of Asparagus officinalis L. as a functional ingredient for nutraceuticals. ETAS possesses heat shock protein 70 (HSP70) induction activity and may contribute to maintenance and improvement of health. Here, 3 compounds (1, 2, 3) were isolated from ETAS. The structures of 1, 2, and 3 were deduced by HREIMS and NMR spectroscopic data, and the compounds were identified as cyclo(l-Phe-l-Pro), cyclo(l-Tyr-l-Pro), and cyclo(l-Leu-l-Pro), respectively. Each compound contained a diketopiperazine ring derived from proline with an alkyl group at C-3; thus, we terme

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26

Bratakos, Sotirios, Panagiotis Zoumpoulakis, Eleni Siapi, Kyriakos Riganakos, and Vassilia Sinanoglou. "Determination of 2,5-Diketopiperazines Iin Greek Processed Olives by Liquid Chromatography/Mass Spectrometry Analysis." Current Research in Nutrition and Food Science Journal 4, Special-Issue-October (2016): 63–76. http://dx.doi.org/10.12944/crnfsj.4.special-issue-october.09.

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Diketopiperazines (DKPs) are cyclic dipeptides which have been detected in a variety of natural products, especially in thermally treated or fermented foods and beverages, providing a metallic bitter taste. DKPs, mainly due to their characteristic heterocyclic system, have been reported to exhibit a broad spectrum of biological activities including antimicrobial, antiviral, antitumor, antihyperglycaemic and antimutagenic. In the present study, several DKPs were identified in seven different Greek varieties of processed olives using HR-LC-MSn. The identification of DKPs in olive samples was ach

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27

Saviano, Michele, Carla Isernia, Filomena Rossi, et al. "Solid state structural analysis of the cyclooctapeptide cyclo- (Pro1-Pro-Phe-Phe-Ac6c-Ile-D-Ala-Val8)." Biopolymers 53, no. 2 (2000): 189–99. http://dx.doi.org/10.1002/(sici)1097-0282(200002)53:2<189::aid-bip9>3.0.co;2-7.

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28

Lee, Seoung Rak, Christine Beemelmanns, Leah M. M. Tsuma, Jon Clardy, Shugeng Cao, and Ki Hyun Kim. "A New Diketopiperazine, Cyclo(D-trans-Hyp-L-Leu) from a Kenyan Bacterium Bacillus licheniformis LB 8CT." Natural Product Communications 11, no. 4 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100410.

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Bacterially-produced small molecules demonstrate a wide range of structural and functional diversity. A new diketopiperazine, cyclo(D- trans-Hyp-L-Leu) (1), and five other known diketopiperazines (2–6), were isolated and purified from the fermented broth of a Kenyan bacterium Bacillus licheniformis LB 8CT. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR and HR-MS, and the absolute configuration was determined by a combination of NOESY analysis and Marfey's method. The known compounds were identified as cyclo(D- cis-Hyp-L-Leu) (2), cyclo(

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29

Sioud, Samiha, Ines Karray-Rebai, Hedi Aouissaoui, Bertrand Aigle, Samir Bejar, and Lotfi Mellouli. "Targeted Gene Disruption of the Cyclo (L-Phe, L-Pro) Biosynthetic Pathway inStreptomycessp. US24 Strain." Journal of Biomedicine and Biotechnology 2007 (2007): 1–9. http://dx.doi.org/10.1155/2007/91409.

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We have previously isolated a new actinomycete strain from Tunisian soil calledStreptomycessp. US24, and have shown that it produces two bioactive molecules including a Cyclo (L-Phe, L-Pro) diketopiperazine (DKP). To identify the structural genes responsible for the synthesis of this DKP derivative, a PCR amplification (696 bp) was carried out using theStreptomycessp. US24 genomic DNA as template and two degenerate oligonucleotides designed by analogy with genes encoding peptide synthetases (NRPS). The detection of DKP derivative biosynthetic pathway of theStreptomycessp. US24 strain was then

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30

Kaakkola, Seppo, and Richard J. Wurtman. "Effects of two diketopiperazines, cyclo (His-Pro) and Cyclo (Asp-Phe), on striatal dopamine: A microdialysis study." Brain Research Bulletin 32, no. 6 (1993): 667–72. http://dx.doi.org/10.1016/0361-9230(93)90171-7.

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31

Fang, Qing, Fleurdeliz Maglangit, Linrui Wu, et al. "Signalling and Bioactive Metabolites from Streptomyces sp. RK44." Molecules 25, no. 3 (2020): 460. http://dx.doi.org/10.3390/molecules25030460.

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Streptomyces remains one of the prolific sources of structural diversity, and a reservoir to mine for novel natural products. Continued screening for new Streptomyces strains in our laboratory led to the isolation of Streptomyces sp. RK44 from the underexplored areas of Kintampo waterfalls, Ghana, Africa. Preliminary screening of the metabolites from this strain resulted in the characterization of a new 2-alkyl-4-hydroxymethylfuran carboxamide (AHFA) 1 together with five known compounds, cyclo-(L-Pro-Gly) 2, cyclo-(L-Pro-L-Phe) 3, cyclo-(L-Pro-L-Val) 4, cyclo-(L-Leu-Hyp) 5, and deferoxamine E

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32

Kessler, H., G. Gemmecker, A. Haupt, M. Klein, K. Wagner, and M. Will. "Alanine containing analogues of cyclo(-d-pro-phe-thr-lys(z)-trp-phe-)- conformationally controlled structure-activity-relationships." Tetrahedron 44, no. 3 (1988): 745–59. http://dx.doi.org/10.1016/s0040-4020(01)86114-7.

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33

Shaala, Lamiaa A., Diaa T. A. Youssef, Torki A. Alzughaibi, and Sameh S. Elhady. "Antimicrobial Chlorinated 3-Phenylpropanoic Acid Derivatives from the Red Sea Marine Actinomycete Streptomyces coelicolor LY001." Marine Drugs 18, no. 9 (2020): 450. http://dx.doi.org/10.3390/md18090450.

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The actinomycete strain Streptomyces coelicolor LY001 was purified from the sponge Callyspongia siphonella. Fractionation of the antimicrobial extract of the culture of the actinomycete afforded three new natural chlorinated derivatives of 3-phenylpropanoic acid, 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid (1), 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid methyl ester (2), and 3-(3-chloro-4-hydroxyphenyl)propanoic acid (3), together with 3-phenylpropanoic acid (4), E-cinnamic acid (5), and the diketopiperazine alkaloids cyclo(l-Phe-trans-4-OH-l-Pro) (6) and cyclo(l-Phe-cis-4-OH-d-Pro) (7)

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34

ISHIZU, Takashi, Ayumi FUJII, and Shunsaku NOGUCHI. "Conformational studies of cyclo(L-Phe-L-Pro-Gly-L-Pro)2 by 13C nuclear magnetic resonance." CHEMICAL & PHARMACEUTICAL BULLETIN 39, no. 6 (1991): 1617–19. http://dx.doi.org/10.1248/cpb.39.1617.

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35

Budesinsky, Milos, Ivana Cisarova, Jaroslav Podlaha, et al. "Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives." Acta Crystallographica Section B Structural Science 66, no. 6 (2010): 662–77. http://dx.doi.org/10.1107/s0108768110040243.

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The crystal structures of eight cyclodipeptides are determined, incorporating pipecolic acid or proline and phenylalanine or N-methyl phenylalanine. This set of structures allows the evaluation of the effects on molecular conformation and crystal packing of imino acid ring-size, relative configuration of the two amino acids, and N-methylation. In the non-methylated compounds, hydrogen-bonding interactions form one-dimensional motifs that dominate the packing arrangement. Three compounds have more than one symmetry-independent molecule in the asymmetric unit (Z′ > 1), indicative of a broad a

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Frikha Dammak, Donyez, Ziad Zarai, Soumaya Najah, et al. "Antagonistic Properties of Some Halophilic Thermoactinomycetes Isolated from Superficial Sediment of a Solar Saltern and Production of Cyclic Antimicrobial Peptides by the Novel Isolate Paludifilum halophilum." BioMed Research International 2017 (2017): 1–13. http://dx.doi.org/10.1155/2017/1205258.

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This study has focused on the isolation of twenty-three halophilic actinomycetes from two ponds of different salinity and the evaluation of their ability to exert an antimicrobial activity against both their competitors and several other pathogens. From the 23 isolates, 18 strains showed antagonistic activity, while 19 showed activities against one or more of the seven pathogen strains tested. Six strains exhibited consistent antibacterial activity against Gram-negative and Gram-positive pathogens characterized at the physiological and molecular levels. These strains shared only 94-95% 16S rRN

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Zanotti, Giancarlo, Filomena Rossi, Michele Saviano, et al. "A potent cyclolinopeptide A analog: Solid state and solution conformation of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2." Journal of the American Chemical Society 117, no. 33 (1995): 8651–58. http://dx.doi.org/10.1021/ja00138a022.

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Rabal Biasetto, Carolina, Andressa Somensi, Fernanda Sales Figueiro, et al. "Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa." Eclética Química Journal 44, no. 3 (2019): 36–42. http://dx.doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42.

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Chemical investigation of the crude PDB extract obtained from the endophytic fungus Schizophyllum commune afforded the pure substances, cyclo(L-Pro-L-Val) (1), uracil (2), cyclo(Pro-Tyr) (3), p-hydroxybenzoic acid (4) and a mixture of Rel.cyclo(Pro-Phe) (5) and Rel.cyclo(Pro-Ile) (6). When cultured in corn, the extract of this fungus yielded N-(2-phenylethyl) acetamide (7) and N-(4-hydroxyphenylethyl) acetamide (8). The structures of all compounds were determined based on the analyses of their MS, 1D and 2D-NMR spectroscopic data. Analysis of the crude extracts obtained from small-scale cultur

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Park, Na-Young, Young Bin Cho, Ok Bin Kim, and Kun-Soo Kim. "Cyclo(Phe-Pro) produced by Vibrio species passes through biological membranes by simple diffusion." Applied Microbiology and Biotechnology 104, no. 15 (2020): 6791–98. http://dx.doi.org/10.1007/s00253-020-10646-4.

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Wang, Guanghua, Shikun Dai, Minjie Chen, et al. "Two diketopiperazine cyclo(pro-phe) isomers from marine bacteria Bacillus subtilis sp. 13-2." Chemistry of Natural Compounds 46, no. 4 (2010): 583–85. http://dx.doi.org/10.1007/s10600-010-9680-8.

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Vázquez-Rivera, Dolores, Omar González, Jaquelina Guzmán-Rodríguez, et al. "Cytotoxicity of Cyclodipeptides fromPseudomonas aeruginosaPAO1 Leads to Apoptosis in Human Cancer Cell Lines." BioMed Research International 2015 (2015): 1–9. http://dx.doi.org/10.1155/2015/197608.

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Pseudomonas aeruginosais an opportunistic pathogen of plants and animals, which produces virulence factors in order to infect or colonize its eukaryotic hosts. Cyclodipeptides (CDPs) produced byP. aeruginosaexhibit cytotoxic properties toward human tumor cells. In this study, we evaluated the effect of a CDP mix, comprised of cyclo(L-Pro-L-Tyr), cyclo(L-Pro-L-Val), and cyclo(L-Pro-L-Phe) that were isolated fromP. aeruginosa, on two human cancer cell lines. Our results demonstrated that the CDP mix promoted cell death in cultures of the HeLa cervical adenocarcinoma and Caco-2 colorectal adenoca

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JOIS, D. S. SEETHARAMA, STEPHEN SURESH M. VIJAYAN, and K. R. K. EASWARAN. "NMR and X-ray crystallographic studies on cyclic tetrapeptide, cyclo (D-Phe-Pro-Sar-Gly)." International Journal of Peptide and Protein Research 48, no. 1 (2009): 12–20. http://dx.doi.org/10.1111/j.1399-3011.1996.tb01102.x.

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Mazzeo, Marco, Carla Isernia, Filomena Rossi, et al. "Conformational behaviour of A cyclolinopeptide a analogue: Two-dimensional NMR study of cyclo(Pro1-Pro-Phe-Phe-Ac6c-IIe-ala-Val8)." Journal of Peptide Science 1, no. 5 (1995): 330–40. http://dx.doi.org/10.1002/psc.310010508.

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Ferracane, Michael J., Ariana C. Brice-Tutt, Jeremy S. Coleman, et al. "Design, Synthesis, and Characterization of the Macrocyclic Tetrapeptide cyclo[Pro-Sar-Phe-d-Phe]: A Mixed Opioid Receptor Agonist–Antagonist Following Oral Administration." ACS Chemical Neuroscience 11, no. 9 (2020): 1324–36. http://dx.doi.org/10.1021/acschemneuro.0c00086.

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KESSLER, H., A. HAUPT, M. SCHUDOK, K. ZIEGLER, and M. FRIMMER. "Peptide conformations - 49(1): Synthesis and structure-activity relationships of side chain modified peptides of cyclo(-d-Pro-Phe-Thr-Lys-Trp-Phe-)." International Journal of Peptide and Protein Research 32, no. 3 (2009): 183–93. http://dx.doi.org/10.1111/j.1399-3011.1988.tb00933.x.

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Asano, Akiko, Shiori Matsuoka, Chisato Minami, Takuma Kato та Mitsinobu Doi. "[Leu2]Gramicidin S preserves the structural properties of its parent peptide and forms helically aligned β-sheets". Acta Crystallographica Section C Structural Chemistry 75, № 10 (2019): 1336–43. http://dx.doi.org/10.1107/s2053229619011872.

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For crystallographic analysis, Leu was substituted for Orn in Gramicidin S (LGS) to suppress interactions with hydrophilic solvent molecules, which increased the flexibility of the Orn side chains, leading to disorder within the crystals. The asymmetric unit (C62H94N10O10·1.296C3H8O·1.403H2O) contains three LGS molecules (A, B and C) forming β-turn and intramolecular β-sheet structures. With the exception of one motif in molecule C, D-Phe-Pro turn motifs (Phe is phenylalanine and Pro is proline) were classed as type II′ β-turns. The peptide backbones twist slightly to the right along the long

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Martínez-Luis, Sergio, Lilia Cherigo, Carmenza Spadafora, and Marcelino Gutiérrez. "Antiparasitic Compounds from the Panamanian Marine Bacterium Pseudomonas aeruginosa." Natural Product Communications 14, no. 1 (2019): 1934578X1901400. http://dx.doi.org/10.1177/1934578x1901400109.

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Fractionation of the ethyl acetate extract of the bacterium Pseudomonas aeruginosa led to the isolation of five compounds, cyclo –(L-Phe-L-Pro) (1), 3-heptyl-3-hydroxy-1,2,3,4-tetrahydroquinoline-2.4-dione (2), 2-heptyl-4-hydroxyquinoline (3), 2-nonyl-4-hydroxyquinoline (4), and 1-phenazinecarboxylic acid (5). The structures of compounds 1-5 were established by spectroscopic analyses. Compounds 2 4 produced inhibition on the growth of Plasmodium falciparum, with IC50 values of 3.47, 2.57 and 2.79 μg/mL, respectively. Compounds 3-4 had activity against Trypanosoma cruzi, with IC50 values of 3.6

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VATER, Joachim, Wilhelm SCHLUMBOHM, Zbigniew PALACZ, Johann SALNIKOW, Andre GADOW, and Horst KLEINKAUF. "Formation of D-Phe-Pro-Val-cyclo-Orn by gramicidin S synthetase in the absence of L-leucine." European Journal of Biochemistry 163, no. 2 (1987): 297–302. http://dx.doi.org/10.1111/j.1432-1033.1987.tb10800.x.

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ISHIZU, Takashi, and Shunsaku NOGUCHI. "Enantiomer-Differentiating Ability of Cyclo(L-Phe-L-Pro)4 Having a Rigid Skeleton for Phenylalanine Methylester Hydrochloride." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 7 (1997): 1202–4. http://dx.doi.org/10.1248/cpb.45.1202.

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ISHIZU, Takashi, and Shunsaku NOGUCHI. "Enantiomer-Differentiating Ability of Cyclo(Phe-Pro)4 for Noradrenaline Hydrochloride and Preparation of Complexes with Various Amine Hydrochlorides." CHEMICAL & PHARMACEUTICAL BULLETIN 46, no. 8 (1998): 1303–7. http://dx.doi.org/10.1248/cpb.46.1303.

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