Fmoc-PEG4-Ala-Ala-Asn-PAB - CAS 2055048-57-0

Fmoc-PEG4-Ala-Ala-Asn-PAB - CAS 2055048-57-0 Catalog number: BADC-01049

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Fmoc-PEG4-Ala-Ala-Asn-PAB is a cleavable 4-unit PEG peptide linker that is used to synthesize antibody-conjugated drugs (ADCs).

Category
ADCs Linker
Product Name
Fmoc-PEG4-Ala-Ala-Asn-PAB
CAS
2055048-57-0
Catalog Number
BADC-01049
Molecular Formula
C43H56N6O12
Molecular Weight
848.95
Purity
≥95%
Fmoc-PEG4-Ala-Ala-Asn-PAB

Ordering Information

Catalog Number Size Price Quantity
BADC-01049 -- $-- Inquiry
Description
Fmoc-PEG4-Ala-Ala-Asn-PAB is a cleavable 4-unit PEG peptide linker that is used to synthesize antibody-conjugated drugs (ADCs).
Synonyms
L-Aspartamide, N-[19-(9H-fluoren-9-yl)-1,17-dioxo-4,7,10,13,18-pentaoxa-16-azanonadec-1-yl]-L-alanyl-L-alanyl-N1-[4-(hydroxymethyl)phenyl]-; N-[1-(9H-Fluoren-9-yl)-3,19-dioxo-2,7,10,13,16-pentaoxa-4-azanonadecan-19-yl]-L-alanyl-L-alanyl-N1-[4-(hydroxymethyl)phenyl]-L-aspartamide; (9H-fluoren-9-yl)methyl ((17S,20S,23S)-25-amino-23-((4-(hydroxymethyl)phenyl)carbamoyl)-17,20-dimethyl-15,18,21,25-tetraoxo-3,6,9,12-tetraoxa-16,19,22-triazapentacosyl)carbamate
IUPAC Name
9H-fluoren-9-ylmethyl N-[2-[2-[2-[2-[3-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[4-(hydroxymethyl)anilino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate
Canonical SMILES
CC(C(=O)NC(C)C(=O)NC(CC(=O)N)C(=O)NC1=CC=C(C=C1)CO)NC(=O)CCOCCOCCOCCOCCNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
InChI
InChI=1S/C43H56N6O12/c1-28(40(53)47-29(2)41(54)49-37(25-38(44)51)42(55)48-31-13-11-30(26-50)12-14-31)46-39(52)15-17-57-19-21-59-23-24-60-22-20-58-18-16-45-43(56)61-27-36-34-9-5-3-7-32(34)33-8-4-6-10-35(33)36/h3-14,28-29,36-37,50H,15-27H2,1-2H3,(H2,44,51)(H,45,56)(H,46,52)(H,47,53)(H,48,55)(H,49,54)/t28-,29-,37-/m0/s1
InChIKey
SAXNVMPCIWDUGW-PBCNQIPESA-N
Density
1.3±0.1 g/cm3
Solubility
Soluble in DMSO
Appearance
White Solid
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Boiling Point
1172.6±65.0°C at 760 mmHg
Form
Solid

Fmoc-PEG4-Ala-Ala-Asn-PAB is a specialized compound utilized in advanced peptide synthesis and drug development applications. The Fmoc (9-fluorenylmethyloxycarbonyl) group protects the N-terminus, enabling controlled peptide chain elongation through solid-phase peptide synthesis (SPPS). This compound combines the hydrophilic PEG4 (tetraethylene glycol) spacer with the Ala-Ala-Asn tripeptide sequence and a para-aminobenzyl (PAB) moiety, making it a versatile building block for constructing functionalized peptides and bioconjugates.

The PEG4 spacer in Fmoc-PEG4-Ala-Ala-Asn-PAB introduces flexibility and solubility to the compound, enhancing the pharmacokinetic properties of peptide conjugates. This hydrophilic segment helps reduce aggregation and improves the stability of peptide-based drugs in aqueous environments. As a result, Fmoc-PEG4-Ala-Ala-Asn-PAB is widely used in the design of peptide-drug conjugates (PDCs) and antibody-drug conjugates (ADCs), where it facilitates the attachment of cytotoxic agents, imaging probes, or targeting ligands. This functionality is particularly beneficial in precision medicine, allowing for targeted drug delivery and reduced off-target effects.

The Ala-Ala-Asn sequence in Fmoc-PEG4-Ala-Ala-Asn-PAB is significant for creating linkers or substrates in protease-sensitive drug delivery systems. This sequence can be engineered to serve as a recognition site for specific enzymes, enabling controlled drug release in target tissues, such as tumors or inflamed regions. Such enzyme-responsive linkers are essential in developing prodrugs and ADCs that activate their therapeutic payloads only in disease-specific environments, minimizing systemic toxicity.

The PAB (para-aminobenzyl) group is another key feature of Fmoc-PEG4-Ala-Ala-Asn-PAB, acting as a self-immolative linker. After enzymatic cleavage of the tripeptide sequence, the PAB moiety undergoes rapid decomposition, releasing the attached drug or bioactive molecule. This unique property makes the compound highly valuable in designing cleavable linkers for ADCs and PDCs, enabling precise and efficient release of therapeutic agents at the desired site of action.

Fmoc-PEG4-Ala-Ala-Asn-PAB is also used in the synthesis of biofunctionalized surfaces and biomaterials. The PEG4 segment ensures compatibility with biological systems, while the peptide sequence and PAB moiety enable the controlled release of immobilized bioactive molecules. These characteristics make the compound an essential tool in drug delivery, biosensing, and the development of smart materials for biomedical applications.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: m-PEG8-Ms | Fmoc-PEG4-Ala-Ala-Asn-PAB
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