PC Methyltetrazine-PEG4-NHS carbonate ester

 CAS No.: 2055736-28-0  Cat No.: BP-500441 4.5  

PC Methyltetrazine-PEG4-NHS carbonate ester is a photocleavable, dual-reactive PEG conjugation reagent. Structurally, it contains a methyltetrazine–PEG4 segment connected to a nitroaryl photocleavable unit bearing an NHS carbonate. The tetrazine acts as an electron-poor diene in IEDDA ligation with TCO or related strained dienophiles, while the NHS carbonate reacts with primary amines to form a carbamate; suitable irradiation can cleave the nitroaryl photolabile linkage. In PROTAC and related targeted protein degradation research, the reagent supports amine installation, catalyst-free tetrazine ligation, and light-triggered release in research probes or modular degrader systems. Its defined architecture allows researchers to evaluate how linker polarity, flexibility, attachment sequence, and terminal-group selection influence conjugate preparation and the spatial requirements of productive target–E3 ligase engagement. Clear assignment of the protected and reactive groups also supports reproducible reaction planning and systematic comparison of alternative linker designs in research-focused targeted protein degradation workflows.

PC Methyltetrazine-PEG4-NHS carbonate ester

Structure of 2055736-28-0

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PROTAC Linker
Molecular Formula
C₃₅H₄₃N₇O₁₄
Molecular Weight
785.75

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
(2,5-dioxopyrrolidin-1-yl) 1-[5-methoxy-4-[4-[2-[2-[2-[2-[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethylamino]-4-oxobutoxy]-2-nitrophenyl]ethyl carbonate
InChI Key
FYXJZLYXHCHOII-UHFFFAOYSA-N
InChI
InChI=1S/C35H43N7O14/c1-23(55-35(46)56-41-32(44)10-11-33(41)45)27-21-29(49-3)30(22-28(27)42(47)48)54-13-4-5-31(43)36-12-14-50-15-16-51-17-18-52-19-20-53-26-8-6-25(7-9-26)34-39-37-24(2)38-40-34/h6-9,21-23H,4-5,10-20H2,1-3H3,(H,36,43)
SMILES
CC1=NN=C(N=N1)C2=CC=C(C=C2)OCCOCCOCCOCCNC(=O)CCCOC3=C(C=C(C(=C3)[N+](=O)[O-])C(C)OC(=O)ON4C(=O)CCC4=O)OC

This PC Methyltetrazine-PEG4-NHS carbonate ester is a bifunctional PROTAC linker designed to couple a methyltetrazine handle with an NHS-activated carbonate for efficient amide/amine-compatible conjugation. Its PEG-based spacer improves solubility and conformational flexibility, supporting productive ternary complex formation in targeted protein degradation workflows. The following points describe its structure and practical reactivity considerations for constructing PROTACs.

Structure: The molecule contains a methyltetrazine moiety linked through a polyethylene glycol spacer to an NHS carbonate ester. It features an NHS-activated carbonate functional group for acyl transfer chemistry and a tetrazine ring suited to bioorthogonal conjugation. The PEG segment provides hydrophilic, flexible connectivity.

Reactivity: The NHS carbonate ester reacts with primary amines under mild aqueous or mixed solvent conditions, typically forming stable amide-linked conjugates via nucleophilic acyl substitution. The methyltetrazine functionality enables rapid tetrazine–dienophile ligation (commonly used in PROTAC assembly) under bioorthogonal conditions compatible with sensitive biomolecules. Use an amine-free buffer for NHS activation, then introduce the amine-bearing partner; protect from strong nucleophiles that can hydrolyze the NHS carbonate.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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