Sulfo DBCO-PEG4-Maleimide - CAS 2055198-07-5

Sulfo DBCO-PEG4-Maleimide is a polyethylene glycol (PEG)-based PROTAC linker. Sulfo DBCO-PEG4-Maleimide can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C₃₉H₄₇N₅O₁₃S
Molecular Weight
825.88

Sulfo DBCO-PEG4-Maleimide

    • Specification
      • Purity
        90%
        Storage
        Please store the product under the recommended conditions in the Certificate of Analysis.
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        1-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-3-[3-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]-1-oxopropane-2-sulfonic acid
        Synonyms
        DBCO-Sulfo-PEG4-Maleimide; 1-[[3-(2-Azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-3-[3-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]-1-oxopropane-2-sulfonic acid
    • Properties
      • InChI Key
        QXLOITKOSRDQIZ-UHFFFAOYSA-N
        InChI
        InChI=1S/C39H47N5O13S/c45-34(14-18-43-36(47)11-12-37(43)48)40-17-20-55-22-24-57-26-25-56-23-21-54-19-15-35(46)42-27-33(58(51,52)53)39(50)41-16-13-38(49)44-28-31-7-2-1-5-29(31)9-10-30-6-3-4-8-32(30)44/h1-8,11-12,33H,13-28H2,(H,40,45)(H,41,50)(H,42,46)(H,51,52,53)
        Canonical SMILES
        C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCNC(=O)C(CNC(=O)CCOCCOCCOCCOCCNC(=O)CCN4C(=O)C=CC4=O)S(=O)(=O)O
    • Reference Reading
      • 1. New mechanisms for bacterial degradation of sulfoquinovose
        Yifeng Wei, Yang Tong, Yan Zhang Biosci Rep. 2022 Oct 28;42(10):BSR20220314.doi: 10.1042/BSR20220314.
        Sulfoquinovose (SQ, 6-deoxy-6-sulfo-D-glucose) is a sulfo-sugar with a ubiquitous distribution in the environment due to its production by plants and other photosynthetic organisms. Bacteria play an important role in degradation of SQ and recycling of its constituent sulfur and carbon. Since its discovery in 1963, SQ was noted to have a structural resemblance to glucose-6-phosphate and proposed to be degraded through a pathway analogous to glycolysis, termed sulfoglycolysis. Studies in recent years have uncovered an unexpectedly diverse array of sulfoglycolytic pathways in different bacteria, including one analogous to the Embden-Meyerhof-Parnas pathway (sulfo-EMP), one analogous to the Entner-Doudoroff pathway (sulfo-ED), and two involving sulfo-sugar cleavage by a transaldolase (sulfo-TAL) and transketolase (sulfo-TK), respectively, analogous to reactions in the pentose phosphate (PP) pathway. In addition, a non-sulfoglycolytic SQ degradation pathway was also reported, involving oxygenolytic C-S cleavage catalyzed by a homolog of alkanesulfonate monooxygenase (sulfo-ASMO). Here, we review the discovery of these new mechanisms of SQ degradation and lessons learnt in the study of new catabolic enzymes and pathways in bacteria.
        2. Differential biotin labelling of the cell envelope proteins in lipopolysaccharidic diderm bacteria: Exploring the proteosurfaceome of Escherichia coli using sulfo-NHS-SS-biotin and sulfo-NHS-PEG4-bismannose-SS-biotin
        Ricardo Monteiro, Ingrid Chafsey, Sabine Leroy, Christophe Chambon, Michel Hébraud, Valérie Livrelli, Mariagrazia Pizza, Alfredo Pezzicoli, Mickaël Desvaux J Proteomics. 2018 Jun 15;181:16-23.doi: 10.1016/j.jprot.2018.03.026.Epub 2018 Mar 30.
        Surface proteins are the major factor for the interaction between bacteria and its environment, playing an important role in infection, colonisation, virulence and adaptation. However, the study of surface proteins has proven difficult mainly due to their hydrophobicity and/or relatively low abundance compared with cytoplasmic proteins. To overcome these issues new proteomic strategies have been developed, such as cell-surface protein labelling using biotinylation reagents. Sulfo-NHS-SS-biotin is the most commonly used reagent to investigate the proteins expressed at the cell surface of various organisms but its use in lipopolysaccharidic diderm bacteria (archetypical Gram-negative bacteria) remains limited to a handful of species. While generally pass over in silence, some periplasmic proteins, but also some inner membrane lipoproteins, integral membrane proteins and cytoplasmic proteins (cytoproteins) are systematically identified following this approach. To limit cell lysis and diffusion of the sulfo-NHS-SS-biotin through the outer membrane, biotin labelling was tested over short incubation times and proved to be as efficient for 1 min at room temperature. To further limit labelling of protein located below the outer membrane, the use of high-molecular weight sulfo-NHS-PEG4-bismannose-SS-biotin appeared to recover differentially cell-envelope proteins compared to low-molecular weight sulfo-NHS-SS-biotin. Actually, the sulfo-NHS-SS-biotin recovers at a higher extent the proteins completely or partly exposed in the periplasm than sulfo-NHS-PEG4-bismannose-SS-biotin, namely periplasmic and integral membrane proteins as well as inner membrane and outer membrane lipoproteins. These results highlight that protein labelling using biotinylation reagents of different sizes provides a sophisticated and accurate way to differentially explore the cell envelope proteome of lipopolysaccharidic diderm bacteria.Significance:While generally pass over in silence, some periplasmic proteins, inner membrane lipoproteins (IMLs), integral membrane proteins (IMPs) and cytoplasmic proteins (cytoproteins) are systematically identified following cell-surface biotin labelling in lipopolysaccharidic diderm bacteria (archetypal Gram-negative bacteria). The use of biotinylation molecules of different sizes, namely sulfo-NHS-SS-biotin and sulfo-NHS-PEG4-bismannose-SS-biotin, was demonstrated to provide a sophisticated and accurate way to differentially explore the cell envelope proteome of lipopolysaccharidic diderm bacteria.
        3. Current Concepts on 6-sulfo LacNAc Expressing Monocytes (slanMo)
        Fareed Ahmad, Thomas Döbel, Marc Schmitz, Knut Schäkel Front Immunol. 2019 May 22;10:948.doi: 10.3389/fimmu.2019.00948.eCollection 2019.
        The human mononuclear phagocytes system consists of dendritic cells (DCs), monocytes, and macrophages having different functions in bridging innate and adaptive immunity. Among the heterogeneous population of monocytes the cell surface marker slan (6-sulfo LacNAc) identifies a specific subset of human CD14- CD16+ non-classical monocytes, called slan+ monocytes (slanMo). In this review we discuss the identity and functions of slanMo, their contributions to immune surveillance by pro-inflammatory cytokine production, and cross talk with T cells and NK cells. We also consider the role of slanMo in the regulation of chronic inflammatory diseases and cancer. Finally, we highlight unresolved questions that should be the focus of future research.
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