Product Name: MC-Ala-Ala-Asn-PAB-PNP
Purity: 95%
Storage : Sealed storage, away from moisture and light, under nitrogen
CAS.NO.: 1638970-45-2
CHEMICAl FORMULA: C34H39N7O12
SMILES: C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)N)C(=O)NC1=CC=C(C=C1)COC(=O)OC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)CCCCCN3C(=O)C=CC3=O
IUPACNAME: [4-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]propanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate
INCHIKEY: UZCNUSRZZPELJW-WOVHNISZSA-N
INCHI: InChI=1S/C34H39N7O12/c1-20(36-28(43)6-4-3-5-17-40-29(44)15-16-30(40)45)31(46)37-21(2)32(47)39-26(18-27(35)42)33(48)38-23-9-7-22(8-10-23)19-52-34(49)53-25-13-11-24(12-14-25)41(50)51/h7-16,20-21,26H,3-6,17-19H2,1-2H3,(H2,35,42)(H,36,43)(H,37,46)(H,38,48)(H,39,47)/t20-,21-,26-/m0/s1
Molar Mass: 737.71
Application: MC-Ala-Ala-Asn-PAB-PNP is a peptide-based linker intermediate used in targeted small-molecule conjugation research. It contains a maleimidocaproyl group for thiol-reactive coupling, an Ala-Ala-Asn peptide sequence, and a PAB-PNP self-immolative activation structure that can support controlled payload attachment and release design. This linker can be used to synthesize specifically activated micromolecular target coupling bodies, making it valuable for drug-linker construction and bioconjugation workflows. MC-Ala-Ala-Asn-PAB-PNP is widely applied in medicinal chemistry, peptide synthesis, targeted drug delivery research, linker optimization, and development of advanced conjugate systems for biomedical applications.
Current Research: Overview MC-Ala-Ala-Asn-PAB-PNP is a peptide-based linker intermediate that can be used to synthesize specifically activated micromolecular target coupling bodies. Structurally, it combines a maleimidocaproyl-type conjugation unit, a short peptide sequence, a PAB self-immolative spacer, and a PNP activated carbonate/ester-type leaving group. Because of this modular structure, MC-Ala-Ala-Asn-PAB-PNP is relevant to research involving targeted small-molecule conjugates, peptide linker chemistry, controlled payload attachment, and bioconjugation design. In modern drug delivery and chemical biology research, linkers are no longer considered passive connectors. They strongly influence conjugate stability, release behavior, solubility, target engagement, and biological activity. MC-Ala-Ala-Asn-PAB-PNP is useful because it contains several functional modules that can support stepwise conjugate assembly. The peptide segment may provide a biologically responsive or sterically defined spacer, the PAB group can serve as a self-immolative release unit, and the PNP group can activate the molecule for coupling with suitable nucleophilic agents. This compound is especially relevant for researchers designing molecules in which a small-molecule agent must be connected to a targeting or carrier component in a controlled manner. Such systems may include targeted drug conjugates, peptide-drug conjugates, antibody-drug conjugate-related intermediates, protein conjugates, ligand-drug conjugates, imaging conjugates, or other molecular delivery platforms. Structural Design of MC-Ala-Ala-Asn-PAB-PNP MC-Ala-Ala-Asn-PAB-PNP contains several important structural components. Each part contributes to its role as a linker intermediate. The MC group, commonly understood as a maleimidocaproyl-type unit, is frequently used in bioconjugation chemistry because maleimides can react with thiol groups. Thiol-reactive chemistry is valuable for coupling linker-payload structures to cysteine-containing peptides, proteins, antibodies, or engineered biomolecules. This makes the MC portion useful when researchers want to connect the linker to a sulfhydryl-containing target or carrier. The Ala-Ala-Asn peptide sequence contains alanine, alanine, and asparagine. Alanine is a small, relatively neutral amino acid that can provide compact spacing without introducing large side-chain bulk. Asparagine contains a polar amide side chain, which may contribute to hydrogen bonding and aqueous compatibility. Together, the Ala-Ala-Asn motif provides a short peptide spacer that may influence linker conformation, enzyme accessibility, and overall conjugate behavior. The PAB group, commonly referring to a p-aminobenzyl-based self-immolative spacer, is frequently used in cleavable linker design. A self-immolative spacer can translate an upstream cleavage or activation event into release of a downstream payload. In many drug-linker systems, peptide cleavage alone may not directly release the active agent. PAB-type spacers help solve this problem by undergoing spontaneous fragmentation after the triggering group is removed. The PNP group, usually associated with p-nitrophenyl activation, is a useful leaving group in synthetic chemistry. PNP-activated intermediates can react with suitable nucleophiles, such as amines or alcohols, to form carbamate, carbonate, or related linkages. In MC-Ala-Ala-Asn-PAB-PNP, the PNP group supports further coupling to a micromolecular agent or payload. Role in Target Coupling Body Synthesis MC-Ala-Ala-Asn-PAB-PNP can be used to synthesize specifically activated micromolecular target coupling bodies. In this context, a “target coupling body” may be understood as a designed conjugate in which a small molecule or functional agent is linked to another targeting, carrier, or recognition component. The compound provides a ready-to-use linker framework for coupling chemistry. The PNP-activated end can participate in attachment to a payload or small-molecule agent, while the MC group can support connection to a thiol-containing biomolecule. This dual-function design allows the linker to bridge two molecular components in a controlled orientation. Such coupling strategies are important because targeted conjugates often require precise architecture. The agent must be attached without destroying its activity. The targeting component must remain capable of recognizing its intended target. The linker must remain stable enough during handling and circulation-like conditions, while also supporting release or activation under the desired biological context. Peptide Linker Function The Ala-Ala-Asn sequence gives MC-Ala-Ala-Asn-PAB-PNP a peptide-based spacer region. Peptide linkers are widely studied because their amino acid sequence can influence flexibility, polarity, protease sensitivity, and spatial organization. Ala-Ala-Asn is short and relatively compact. The two alanine residues can provide a small hydrophobic-neutral backbone segment, while asparagine introduces polarity. This type of peptide spacer may be useful when researchers want a linker that is less bulky than long PEG-based spacers but more structurally defined than simple alkyl chains. Peptide linkers may also be designed for enzymatic processing. Whether Ala-Ala-Asn functions as a cleavable sequence depends on the full conjugate structure and the biological system being tested. For accurate product copy, it is best to describe MC-Ala-Ala-Asn-PAB-PNP as a peptide-based linker intermediate rather than claiming a specific cleavage mechanism unless experimentally validated. PAB-PNP Chemistry and Controlled Payload Attachment The PAB-PNP portion is a key feature of MC-Ala-Ala-Asn-PAB-PNP. The PAB spacer provides a self-immolative unit, while PNP activation enables coupling to appropriate agents. In drug-linker synthesis, PNP-activated intermediates are commonly used to form linkages with payloads containing amino or hydroxyl groups. After coupling, the payload becomes connected through a chemically defined bond. If the upstream peptide-spacer system is designed to be cleaved or activated, the PAB group may then promote payload release through self-immolation. This design is useful in targeted delivery systems where payload release must be controlled. A conjugate that releases its payload too early may cause nonspecific toxicity or poor selectivity. A conjugate that fails to release its payload may show reduced activity. PAB-containing linkers help researchers tune the relationship between linker cleavage and agent release. Potential Applications in Current Research MC-Ala-Ala-Asn-PAB-PNP may be used in several research areas involving targeted conjugate synthesis and linker optimization. In small-molecule target coupling, it can help connect a micromolecular agent to a target-binding or carrier structure. In drug-linker synthesis, it may serve as an intermediate for attaching payloads through PNP-mediated coupling chemistry. In peptide-drug conjugate research, the Ala-Ala-Asn-PAB structure may be used to evaluate how peptide sequence and self-immolative spacing affect release behavior. In ADC-related linker development, the MC group may support thiol-based conjugation strategies, while the PAB-PNP region supports payload installation. In chemical biology, MC-Ala-Ala-Asn-PAB-PNP may be useful for constructing probes, targeted agents, or functional conjugates that require controlled molecular assembly. In structure-activity relationship studies, researchers may compare Ala-Ala-Asn-containing linkers with other peptide motifs to determine how linker sequence affects solubility, stability, release kinetics, and biological activity. Research Considerations Researchers using MC-Ala-Ala-Asn-PAB-PNP should consider several important factors. First, the compound is a linker intermediate, not a complete therapeutic molecule. Its function depends on the final conjugate structure, including the coupled agent, targeting component, and attachment chemistry. Second, the PNP activated group is reactive and may be sensitive to moisture, hydrolysis, or competing nucleophiles. Reaction conditions should be optimized to preserve coupling efficiency and minimize side products. Third, the maleimide-containing MC group is useful for thiol coupling but requires careful control of pH and reducing conditions. Maleimide-thiol conjugation can be affected by thiol oxidation, excess reducing agents, and reaction buffer composition. Fourth, the PAB self-immolative mechanism depends on the complete linker-payload architecture. PAB behavior should be validated after payload coupling because the downstream bond and payload structure influence release. Fifth, the Ala-Ala-Asn peptide segment may influence solubility, protease accessibility, and spacing, but its biological processing should not be assumed without direct testing. Analytical methods such as HPLC, LC-MS, NMR, peptide mapping, stability assays, and release assays may be used to confirm identity, purity, coupling efficiency, and linker performance. For protein or antibody conjugates, additional methods such as SDS-PAGE, size-exclusion chromatography, hydrophobic interaction chromatography, and drug-to-carrier ratio analysis may be required. Future Research Directions As targeted drug delivery and molecular conjugation technologies advance, demand is increasing for linker intermediates that combine specific coupling chemistry with controlled release potential. MC-Ala-Ala-Asn-PAB-PNP fits into this trend by offering a modular design that can support thiol conjugation, peptide-based spacing, self-immolative release, and activated payload coupling. Future studies may evaluate MC-Ala-Ala-Asn-PAB-PNP-derived conjugates with different payload classes, including cytotoxic agents, imaging probes, immune-modulating molecules, enzyme inhibitors, or targeted small molecules. Researchers may also compare this linker with Val-Cit-PAB, GGFG-PAB, Ala-Ala-PAB, PEGylated linkers, and non-cleavable linkers to determine how sequence and spacer design influence conjugate function. In addition, this type of linker may be useful in the development of more precise targeted micromolecular delivery systems. By optimizing linker stability, release rate, and coupling selectivity, researchers can design conjugates with improved activity and reduced nonspecific effects. Conclusion MC-Ala-Ala-Asn-PAB-PNP is a peptide-based linker intermediate that can be used to synthesize specifically activated micromolecular target coupling bodies. Its structure combines an MC conjugation unit, an Ala-Ala-Asn peptide spacer, a PAB self-immolative group, and a PNP activated coupling group. In current research, MC-Ala-Ala-Asn-PAB-PNP is valuable for targeted conjugate synthesis, drug-linker construction, peptide-drug conjugate development, and bioconjugation studies. Its modular design supports controlled attachment of small-molecule agents and potential integration into larger targeting systems. As research in targeted delivery and chemical biology continues to expand, linker intermediates such as MC-Ala-Ala-Asn-PAB-PNP will remain important tools for building more selective and functional molecular conjugates.
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