t-Boc-N-amido-PEG1-acetic acid

 CAS No.: 142929-49-5  Cat No.: BP-501135  Purity: 98% 4.5  

t-Boc-N-amido-PEG1-acetic acid is a PEG-based linker building block featuring a terminal acetic acid functionality and a short, monodisperse oligo(ethylene glycol) spacer that is terminated for subsequent amide coupling. Structurally, it combines a protected amine (t-Boc) with an amide-forming handle, enabling controlled conjugation to ligands used in targeted protein degradation platforms. In PROTAC construction, such PEG linkers are commonly employed to tune the effective distance and relative orientation between the two binding moieties, improving productive ternary complex formation while maintaining sufficient aqueous solubility and reducing nonspecific hydrophobic interactions. The acetic acid terminus provides a convenient site for coupling to activated derivatives of warheads or E3 ligase–recruiting ligands, whereas the protected amine supports stepwise synthesis to minimize side reactions. As a compact PEG linker, it is valuable for optimizing linker length, flexibility, and physicochemical properties during iterative PROTAC design and structure–activity studies.

t-Boc-N-amido-PEG1-acetic acid

Structure of 142929-49-5

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Category
PROTAC Linker
Molecular Formula
C9H17NO5
Molecular Weight
219.23
Related CAS
<a href="/product/boc-aea-dcha-cas-3080047-42-0-101423.html">3080047-42-0</a> (DCHA salt)
Appearance
Colorless to light yellow solid

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

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Purity
98%
Appearance
Colorless to light yellow solid
Storage
Store at -20 °C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]acetic acid
Synonyms
2-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethoxy]acetic acid; 2-(2-((tert-Butoxycarbonyl)amino)ethoxy)acetic acid; 2-(2-[[(tert-Butoxy)carbonyl]amino]ethoxy)acetic acid; 2-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]ethoxy]acetic acid; Boc-5-amino-3-oxapentanoic acid; Boc-2-(2-aminoethoxy)acetic acid; 5-(t-Butyloxycarbonyl-amino)-3-oxapentanoic acid; Boc-AEA; N-Boc-2-(2-aminoethoxy)acetic Acid; t-Boc-N-amido-PEG1-CH2CO2H; (2-Boc-Aminoethoxy)acetic acid; BocNH-PEG1-acid
Boiling Point
391.2±22.0 °C at 760 mmHg
Density
1.151±0.06 g/cm3
InChI Key
UPBQMAHYLWJGDW-UHFFFAOYSA-N
InChI
InChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-4-5-14-6-7(11)12/h4-6H2,1-3H3,(H,10,13)(H,11,12)
SMILES
CC(C)(C)OC(=O)NCCOCC(=O)O

This t-Boc-N-amido-PEG1-acetic acid linker is designed for constructing PROTAC architectures that require a chemically addressable, amide-bearing PEG element to tune solubility and spatial presentation of binding motifs. Its protected amine functionality enables stepwise conjugation strategies, while the carboxylic acid provides a reliable handle for coupling to targeting ligands. The following sections describe its structure and practical reactivity considerations in detail.

Structure: The molecule contains a tert-butoxycarbonyl-protected amide-forming nitrogen linked to a short ethylene glycol unit and a terminal acetic acid moiety. It features stable amide and ether linkages, with a Boc carbamate that can be removed under controlled conditions. Overall polarity supports aqueous compatibility.

Reactivity: The Boc-protected amine supports orthogonal, stepwise synthesis: deprotection followed by amide bond formation to attach PROTAC ligands. Carboxylic acid coupling is typically performed using standard peptide-coupling reagents under mild base conditions in polar organic solvents, forming robust amide linkages via activation of the acid. Careful control of pH and protecting-group stability helps preserve the linker during sequential assembly.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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