400-998-5282
专注多肽 服务科研
400-998-5282
专注多肽 服务科研
Minamiura等人通过细菌蛋白酶从酪蛋白水解液中分离出二酮哌嗪环（Leu Trp）。它是奶酪中检测到的苦味化合物之一。
编号：132418
CAS号：15136-34-2
单字母：cyclo(LW)(main chain cyclo)
| 编号: | 132418 |
| 中文名称: | 环二肽cyclo(Leu-Trp) |
| 中文同义词: | cyclo(Trp-Leu)(main chain cyclo) |
| 英文名: | c(Leu-Trp) |
| 英文同义词: | c(Trp-Leu)、cyclo(Trp-Leu) |
| CAS号: | 15136-34-2 |
| 单字母: | cyclo(LW)(main chain cyclo) |
| 三字母: | cyclo(Leu-Trp)(main chain cyclo) |
| 氨基酸个数: | 2 |
| 分子式: | C17H21N3O2 |
| 平均分子量: | 299.37 |
| 精确分子量: | 299.16 |
| 等电点(PI): | - |
| pH=7.0时的净电荷数: | 0.97 |
| 平均亲水性: | -2.6 |
| 疏水性值: | 1.45 |
| 外观与性状: | 白色粉末状固体 |
| 消光系数: | 5500 |
| 来源: | 人工化学合成，仅限科学研究使用，不得用于人体。 |
| 纯度: | 95%、98% |
| 盐体系: | 可选TFA、HAc、HCl或其它 |
| 生成周期: | 2-3周 |
| 修饰类型: | 酰胺键成环 |
| 储存条件: | 负80℃至负20℃ |
| 标签: | 200+种环二肽现货 现货多肽 |
| 参考文献（References）: | 1. Solov'eva, T.F., Baskunov, B.P., Nefedova, M.Y., et al . Biosynthesis of leucyl- tryptophanyl- diketopiperazine by a culture of Penicillium aurantio- virens and the characteristics of its production . Mikrobiol. 58(3), 393-399 (1989) . <ALLPEPTIDE>2. Kumar, S.N., Mohandas, C., and Nambisan, B. Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human- pathogenic bacteria . Peptides 53(2014), 48-58 (2014) . <ALLPEPTIDE>3. Furukawa, T., Akutagawa, T., Funatani, H., et al . Cyclic dipeptides exhibit potency for scavenging radicals . Bioorg. Med. Chem. 20(6), 2002-2009 (2012) . <ALLPEPTIDE>4. Naim, M., Nir, S., Spielman, A.I., et al . Hypothesis of receptor- dependent and receptor- independent mechanisms for bitter and sweet taste transduction: Implications for slow taste onset and lingering aftertaste . Chemistry of Taste 825, 2–17 (2002) . <ALLPEPTIDE>5. Zubare-Samuelov, M., Peri, I., Tal, M., et al . Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and α2- adrenergic receptors in Xenopus laevis melanophores . Am. J. Physiol. Cell Physiol. 285(5), C1255-1262 (2003) . |
| 溶解度: | Methanol: Soluble |
| SMILES: | O=C([C@H](CC(C)C)N1)N[C@@H](CC2=CNC3=C2C=CC=C3)C1=O |
| InChI/InChI Code: | InChI=1S/C17H21N3O2/c1-10(2)7-14-16(21)20-15(17(22)19-14)8-11-9-18-13-6-4-3-5-12(11)13/h3-6,9-10,14-15,18H,7-8H2,1-2H3,(H,19,22)(H,20,21)/t14-,15-/m0/s1 |
| InChI Key: | BZUNCDPEEKFTCX-GJZGRUSLSA-N |
| Formal Name: | 3S-(1H-indol-3-ylmethyl)-6S-(2-methylpropyl)-2,5-piperazinedione |
The diketopiperazine cyclo(Leu-Trp) has been isolated by Minamiura et al. from casein hydrolyzate by bacterial proteinase. It is one of the bitter compounds detected in cheese.
Cyclo(-Leu-Trp) is a sweetener that has been used in the food industry for many years. Cyclo(-Leu-Trp) is able to bind with quinine and form a complex that can be detected using analytical methods. Cyclo(-Leu-Trp) has been investigated as a ligand that may be able to bind to receptors on cancer cells, which could lead to new treatments for cancer. Cyclo(-Leu-Trp) also has amphipathic properties and can form liposomes at high concentrations. This molecule has also been studied for its ability to induce transduction of DNA into bacterial cells and cellular thermogenesis.
环亮氨酸色氨酸二酮哌嗪源自青霉菌，具备广谱抑菌抑真菌活性，可清除羟基自由基，带有苦味并可快速穿透味觉细胞，同时能激活爪蟾黑色素细胞褪黑素受体，抑制环磷酸腺苷生成，该效果可被褪黑素受体拮抗剂阻断。
Cyclo(L-Leu-L-Trp) is a diketopiperazine metabolite originally isolated from Penicillium . It is active against various bacteria (MICs = 125-1000 µg/ml) and fungi (MICs = 8-64 µg/ml), and it inhibits the production rate of hydroxy radicals in an electron spin resonance (ESR) spectroscopy-based assay (IC = 1.8 µM). Cyclo(L-Leu-L-Trp) is a bitter tastant that can rapidly permeate rat taste cell membranes ex vivo when used at a concentration of 1 mM. It also acts as a melatonin receptor agonist in X. laevis melanophores, inhibiting cAMP accumulation when used at a concentration of 20 µM, an effect that is blocked by the melatonin receptor antagonist luzindole (Item No. 15998 ).
环二肽又叫2,5-二酮哌嗪的衍生物,作为环肽成员中最小的一类环肽，专肽生物有部分环二肽的现货，也可以根据实验需求，定制含D型与L型，S与R构型的氨基酸。
T.Shiba et al., Biopolymers, 20, 1985 (1981)；http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=7306670
N.Minamiura et al., J. Biochem., 72, 841 (1972)；http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=4630112
