CAS: 4289-98-9; Formyl-L-Methionine

该化合物是一种氨基酸衍生物,其特征是附于甲基硫素侧链氮的气态基体组,是一种自然形成的化合物,在蛋白合成中发挥着关键作用,特别是在开始对丙烯酸进行翻译方面.该化学基体组的存在增强了氨基酸与血清的结合性,便利了聚虫合成的开始.N-Formymethionine通常在细菌蛋白中找到,并且被肋骨机器确认为翻译过程中的第一个氨基酸.其结构包括侧链中的硫磺,这是甲基苯的特征.就溶性而言,N-Formymemephine在水中一般是可溶性,因此适合各种生物化学应用.此外,它还涉及蛋白质合成的研究以及翻译启动机制的研究.

结构式图片

欧盟法规

C&L通报

上下游产品

CAS号4309-82-4 N-甲酰基-DL-蛋氨酸 | CAS号64-18-6 甲酸 | CAS号63-68-3 L-蛋氨酸 | CAS号2258-42-6 甲乙酐 | CAS号357-57-3 马钱子碱 | CAS号63-68-3 L-蛋氨酸 | CAS号63472-90-2 2-异氰基-4-(甲硫基)丁酸甲酯

合成工艺路线路线简述

    📜N-甲酰基-Dl-蛋氨酸置于马钱子碱体系中,化学反应生成 N-甲酰-L-蛋氨酸
    参考文献:Windus; Marvel,Journal Of The American Chemical Society,1931,Vol. 53,P. 3493
    标题:Windus; Marvel,Journal Of The American Chemical Society,1931,Vol. 53,P. 3493

    海关参考信息

    专利信息


    专利号:US-5977301-A
    优先权日:1992-09-24
    标题 :Synthesis of N-substituted oligomers
    发明人:ZUCKERMAN RONALD N; KERR JANICE M; KENT STEPHEN B H; MOOS WALTER H; SIMON REYNA J; GOFF DANE A
    权利人:CHIRON CORP
    摘要:A solid-phase method for the synthesis of N-substituted oligomers, such as poly (N-substituted glycines) (referred to herein as poly NSGs) is used to obtain oligomers, such as poly NSGs of potential therapeutic interest which poly NSGs can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two 'sub-monomers' directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a resin-bound alpha -haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability.

    专利号:EP-0671928-B1
    优先权日:1992-09-24
    标题 :Synthesis of n-substituted oligomers
    发明人:ZUCKERMANN RONALD N; KERR JANICE M; KENT STEPHEN BRIAN HENRY; MOOS WALTER H; SIMON REYNA J; GOFF DANE A
    权利人:CHIRON CORP
    摘要:Poly N-substituted Glycines (poly NSGs), wherein the substituents bear purine or pyrimidine bases (R<9>) every second glycine: In addition, a solid phase method for the synthesis of N-substituted oligomers of more general structures is disclosed.The poly NSGs obtainable by this method can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two 'sub-monomers' directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a resin-bound alpha -haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using the automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability.

    专利号:US-5877278-A
    优先权日:1992-09-24
    标题:Synthesis of N-substituted oligomers
    发明人:ZUCKERMANN RONALD N; GOFF DANE A; NG SIMON; SPEAR KERRY; SCOTT BARBARA O; SIGMUND AARON C; GOLDSMITH RICHARD A; MARLOWE CHARLES K; PEI YAZHONG; RICHTER LUTZ; SIMON REYNA
    权利人:CHIRON CORP
    摘要:A solid-phase method for the synthesis of N-substituted oligomers, such as poly (N-substituted glycines) (referred to herein as poly NSGs) is used to obtain oligomers, such as poly NSGs of potential therapeutic interest which poly NSGs can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two 'sub-monomers' directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a solid support-bound alpha -haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability. Combinatorial libraries of cyclic compounds are disclosed wherein the cyclic compounds are comprised of at least one ring structure derived from cyclization of a peptoid backbone. The diversity of product compounds is generated by the sequential addition of substituted submonomers. The combinatorial library includes 10 or more, preferably 100 or more, and more preferably 1,000 or more distinct and different compounds. The library includes each of the product compounds in retrievable and analyzable amounts and preferably includes at least one biologically active compound. Methods of synthesizing the combinatorial libraries and assay devices produced using the libraries are disclosed as is methodology for screening for and obtaining biologically active cyclic organic compounds.

    专利号:WO-9105050-A1
    优先权日:1989-09-29
    标题 :Synthesis of mature human parathyroid hormone
    发明人:SUNG WING L
    权利人:CANADA MAJESTY IN RIGHT OF
    摘要:A nucleotide coding sequence for human parathyroid hormone has been synthesized, which sequence results in a substantially higher yield of mature PTH than hitherto could be obtained. This is achieved by providing a synthesized nucleotide sequence coding for mature human PTH or a biologically active analog, wherein the amino terminal coding sequence is adenine-rich. A sequence wherein the degenerate codons for some or all of amino acids 1 through 5 are adenine-rich is preferred.

    专利号:WO-0037486-A1
    优先权日:1998-12-22
    标题:Synthesis and recovery of aspartame involving enzymatic deformylation step
    发明人:QUAEDFLIEG PETER JAN LEONARD M; SONKE THEODORUS; WAGNER ADOLF FRITZ VOLKER
    权利人:HOLLAND SWEETENER CO; QUAEDFLIEG PETER JAN LEONARD M; SONKE THEODORUS; WAGNER ADOLF FRITZ VOLKER
    摘要:The invention relates to the synthesis of aspartame involving enzymatic deformylation of an N-formyl-α-L-aspartyl-L-phenylalanine compound by treatment with an enzyme having formylmethionyl peptide deformylase activity and having as a co-factor group 5 to 11 bivalent metal ions. The invention also relates to selective preparation and recovery of aspartame from a mixture of N-formyl-α- and β-L-aspartyl-L-phenylalanine compounds by treatment with such enzyme. And finally, the invention relates to one-pot enzymatic synthesis of aspartame from N-formyl-L-aspartic acid and L- or D,L-phenylalanine methyl ester involving an enzymatic deformylation reaction simultaneously with an enzymatic coupling reaction, as well as to one-pot di- or oligopeptide synthesis by simultaneous enzymatic coupling and deformylation reactions in general.

    专利号:WO-2024199465-A1
    优先权日:2023-03-30
    标 题:Unnatural amino acid in cellulo synthesis for site-specific protein modification
    发明人:CHAN MICHAEL KENNETH; LEE MARIANNE; CHENG JIAHUI
    权利人:UNIV HONG KONG CHINESE
    摘要:Provided are genetically modified host cells containing engineered enzymes that support the synthesis of unnatural amino acids, such as D-Cys-ε-Lys, and the incorporation of such unnatural amino acids into a newly synthesized protein. These cells are therefore capable of in vivo or in cellulo synthesis of a protein containing one or more unnatural amino acids strategically placed at pre-determined locations for site-specific modification of the protein. Also provided are the corresponding methods for in vivo synthesis of modified proteins as well as the modified proteins produced by the method.

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Ploss A, Tran A, Menet E, Leiner I, Pamer EG. Cross-recognition of N-formylmethionine peptides is a general characteristic of H2-M3-restricted CD8+ T cells. Infect Immun. 2005 Jul;73(7):4423-6.
    2: Tang J, Hernández G, LeMaster DM. Increased peptide deformylase activity for N-formylmethionine processing of proteins overexpressed in Escherichia coli: application to homogeneous rubredoxin production. Protein Expr Purif. 2004 Jul;36(1):100-5. doi: 10.1016/j.biosystems.2009.05.009. Epub 2009 Jun 6. doi: 10.1186/1471-2180-13-7.
    6: Matheson M, McClean M, Rynell AC, Berend N. Methylprednisolone reduces airway microvascular permeability but not airway resistance induced by N-formylmethionine leucyl-phenylalanine in the rabbit. Respirology. 2004 Jun;9(2):211-4.

    合成参考文献


    摘要:Faber, K.; Glueck, S. M., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 441.
    📝 需求与反馈
    尽可能描述清楚需求与问题信息
    ×

    通知