马尔弗菌素A的结构与合成。
The structure and synthesis of malformin A.
作者信息
Bodanszky M, Stahl G L
出版信息
Proc Natl Acad Sci U S A. 1974 Jul;71(7):2791-4. doi: 10.1073/pnas.71.7.2791.
Abstract
A structure (the disulfide form of cyclo-D-cysteinyl-L-valyl-D-cysteinyl-D-leucyl-L-isoleucyl), previously proposed for malformin A, was reexamined. On the basis of chemical degradations, a different structure (the disulfide form of cyclo-D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-isoleucyl) was established. Accordingly, a compound with this structure was synthesized and was found to be identical with malformin A. The synthetic product causes curvatures on corn roots; maximum effect was seen at a concentration of 0.1 mug/ml, the optimal concentration for malformin A.
摘要
曾被认为是缩苹果菌素A的一种结构（环-D-半胱氨酰-L-缬氨酰-D-半胱氨酰-D-亮氨酰-L-异亮氨酰的二硫形式）被重新研究。基于化学降解，确定了一种不同的结构（环-D-半胱氨酰-D-半胱氨酰-L-缬氨酰-D-亮氨酰-L-异亮氨酰的二硫形式）。因此，合成了具有这种结构的化合物，发现它与缩苹果菌素A相同。该合成产物会使玉米根产生弯曲；在浓度为0.1微克/毫升时观察到最大效应，这是缩苹果菌素A的最佳浓度。
相似文献
1
The structure and synthesis of malformin A.马尔弗菌素A的结构与合成。
Proc Natl Acad Sci U S A. 1974 Jul;71(7):2791-4. doi: 10.1073/pnas.71.7.2791.
2
Synthesis and biological activity of enantio-(5-valine)malformin, a palindrome peptide.回文肽对映体 -（5 - 缬氨酸）马弗菌素的合成与生物活性
J Am Chem Soc. 1975 May 14;97(10):2857-9. doi: 10.1021/ja00843a041.
3
Allomalformin.别马来菌素
Int J Pept Protein Res. 1982 Jul;20(1):16-25.
4
A biomimetic strategy in the synthesis and fragmentation of cyclic protein.一种用于环状蛋白质合成与裂解的仿生策略。
Protein Sci. 1998 Jul;7(7):1583-92. doi: 10.1002/pro.5560070712.
5
Structure-activity relationship of cyclic pentapeptide malformins as fibrinolysis enhancers.环状五肽畸形菌素作为纤溶增强剂的构效关系
Bioorg Med Chem Lett. 2016 Nov 1;26(21):5267-5271. doi: 10.1016/j.bmcl.2016.09.045. Epub 2016 Sep 16.
6
Structure of malformin B, a phytotoxic metabolite produced by Aspergillus niger.黑曲霉产生的具有植物毒性的代谢产物马尔弗菌素B的结构。
Biosci Biotechnol Biochem. 1993 May;57(5):787-91. doi: 10.1271/bbb.57.787.
7
Conformational study of two linear hexapeptides by two-dimensional NMR and computer-simulated modeling: implication for peptide cyclization in solution.通过二维核磁共振和计算机模拟建模对两种线性六肽进行构象研究：对溶液中肽环化的启示
Biochem Biophys Res Commun. 1996 Feb 15;219(2):572-9. doi: 10.1006/bbrc.1996.0275.
8
Design, synthesis, and biological evaluation of new cyclic disulfide decapeptides that inhibit the binding of AP-1 to DNA.抑制AP-1与DNA结合的新型环状二硫键十肽的设计、合成及生物学评价
J Med Chem. 2004 Aug 12;47(17):4239-46. doi: 10.1021/jm049890+.
9
Cyclic hexapeptides bearing carboxyl groups. Interaction with metal ions and lipid membrane.
Int J Pept Protein Res. 1989 Aug;34(2):97-103.
10
Amino-acids and peptides Part XVI. Synthesis of cyclo-[L-(alpha-amino)-beta-alanylglycyl-D-(alpha-amino)-beta-alanylglycyl] and related fourteen-membered cyclotetrapeptides.
J Chem Soc Perkin 1. 1976(19):2010-3. doi: 10.1039/p19760002010.
引用本文的文献
1
Genome-Scale CRISPR/Cas9 Screening Reveals Squalene Epoxidase as a Susceptibility Factor for Cytotoxicity of Malformin A1.基于基因组规模的 CRISPR/Cas9 筛选揭示角鲨烯环氧化酶是马拉硫磷 A1 细胞毒性的易感性因素。
Chembiochem. 2019 Jun 14;20(12):1563-1568. doi: 10.1002/cbic.201800769. Epub 2019 Apr 18.
2
Involvement of RSK1 activation in malformin-enhanced cellular fibrinolytic activity.RSK1 的激活参与了马拉啡增强的细胞纤维蛋白溶解活性。
Sci Rep. 2018 Apr 3;8(1):5472. doi: 10.1038/s41598-018-23745-0.
3
Study of Malformin C, a Fungal Source Cyclic Pentapeptide, as an Anti-Cancer Drug.真菌来源的环五肽马拉弗菌素C作为抗癌药物的研究。
PLoS One. 2015 Nov 5;10(11):e0140069. doi: 10.1371/journal.pone.0140069. eCollection 2015.
4
Phytochrome involvement in the induction of resistance to dark abscission by malformin.植物色素在植物素诱导暗脱落抗性中的作用。
Planta. 1978 Jan;141(3):311-4. doi: 10.1007/BF00388349.
5
Amino acid racemization in Pseudomonas putida KT2440.假单胞菌属 KT2440 中的氨基酸外消旋化。
J Bacteriol. 2013 Nov;195(22):5016-24. doi: 10.1128/JB.00761-13. Epub 2013 Aug 30.
6
Induction of resistance to dark abscission by malformin in white light.白光下马来菌素诱导对暗脱落的抗性。
Plant Physiol. 1978 Aug;62(2):264-6. doi: 10.1104/pp.62.2.264.
7
Phytochrome involvement in stimulation and alleviation of inhibition of plant growth by malformin.光敏色素参与了马来菌素刺激和缓解植物生长抑制的过程。
Plant Physiol. 1977 Oct;60(4):622-4. doi: 10.1104/pp.60.4.622.
8
White light requirements for stimulation of plant growth by malformin.马来菌素刺激植物生长的白光要求。
Plant Physiol. 1977 Jun;59(6):1051-4. doi: 10.1104/pp.59.6.1051.
9
Rhizobins, a group of peptides in the free-amino-Acid pool of the soybean-Rhizobium system.大豆-根瘤菌系统游离氨基酸池中的一组肽类物质，称为根瘤素。
Appl Environ Microbiol. 1986 Mar;51(3):457-61. doi: 10.1128/aem.51.3.457-461.1986.
10
Physiological comparison of D-cysteine desulfhydrase of Escherichia coli with 3-chloro-D-alanine dehydrochlorinase of Pseudomonas putida CR 1-1.
Arch Microbiol. 1988;149(5):413-6. doi: 10.1007/BF00425580.
本文引用的文献
1
Studies on response of bean seedlings & corn roots to malformin.菜豆幼苗和玉米根对玉米赤霉烯酮的反应研究。
Plant Physiol. 1961 Jan;36(1):37-43. doi: 10.1104/pp.36.1.37.
2
Isolation & characterization of malformin.麦芽福菌素的分离与特性分析
Plant Physiol. 1961 Jan;36(1):30-6. doi: 10.1104/pp.36.1.30.
3
Curvatures and Malformations in Bean Plants Caused by Culture Filtrate of Aspergillus niger.黑曲霉培养滤液导致菜豆植株的弯曲和畸形
Plant Physiol. 1958 Jan;33(1):17-22. doi: 10.1104/pp.33.1.17.
4
Preferential release of aspartic acid during the hydrolysis of proteins.蛋白质水解过程中天冬氨酸的优先释放。
Nature. 1950 Jan 14;165(4185):62. doi: 10.1038/165062a0.
5
Synthesis of peptides by aminolysis of nitrophenyl esters.通过硝基苯酯的氨解反应合成肽。
Nature. 1955 Apr 16;175(4459):685. doi: 10.1038/175685a0.
6
Root curvatures induced by culture filtrates of Aspergillus niger.黑曲霉培养滤液诱导的根曲率
Science. 1958 Sep 19;128(3325):661-2. doi: 10.1126/science.128.3325.661.
7
Antibiotic properties of malformin.麦佛明的抗菌特性
Appl Microbiol. 1966 May;14(3):475-6. doi: 10.1128/am.14.3.475-476.1966.
8
[Structure of malformin. II. Synthesis of homodetic cyclic peptides].[马尔福霉素的结构。II. 同系环肽的合成]
Justus Liebigs Ann Chem. 1970 Dec;742:68-73. doi: 10.1002/jlac.19707420109.
9
[Syntheses of malformin and related analogues].
Chem Ber. 1970;103(10):3159-65. doi: 10.1002/cber.19701031019.
10
[Synthesis of a cyclic cystine-peptide with the activity of malformin].[具有缩苹果菌素活性的环胱氨酸肽的合成]
Naturwissenschaften. 1969 Oct;56(10):516. doi: 10.1007/BF00601977.
Zotero 插件