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Fmoc-Lys(Pal-Glu-OtBu)-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Fmoc-Lys(Pal-Glu-OtBu)-OH is a non-cleavable ADC linker. It can also be used as an alkyl chain-based PROTAC linker.

Category

Fmoc-Amino Acids

Catalog number

BAT-001951

CAS number

1491158-62-3

Molecular Formula

C46H69N3O8

Molecular Weight

792

IUPAC Name

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(4S)-4-(hexadecanoylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]hexanoic acid

Synonyms

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-6-[[(4S)-4-(hexadecanoylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]hexanoic acid; Fmoc-l-lys(palm-l-glu-otbu)-OH

Appearance

White to off-white solid

Density

1.099±0.06 g/cm3

Boiling Point

944.2±65.0 °C(Predicted)

InChI

InChI=1S/C46H69N3O8/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-29-42(51)48-40(44(54)57-46(2,3)4)30-31-41(50)47-32-23-22-28-39(43(52)53)49-45(55)56-33-38-36-26-20-18-24-34(36)35-25-19-21-27-37(35)38/h18-21,24-27,38-40H,5-17,22-23,28-33H2,1-4H3,(H,47,50)(H,48,51)(H,49,55)(H,52,53)/t39-,40-/m0/s1

InChI Key

LQQXBYSAGYOQJW-ZAQUEYBZSA-N

Canonical SMILES

CCCCCCCCCCCCCCCC(=O)NC(CCC(=O)NCCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C

Fmoc-Lys(Pal-Glu-OtBu)-OH is a specialized peptide essential for crafting intricate biomolecules and pharmaceuticals.

Peptide Synthesis: Widely employed in peptide synthesis, Fmoc-Lys(Pal-Glu-OtBu)-OH plays a pivotal role in the chemical assembly of peptides, especially for introducing specific modifications or functional groups. Its protected lysine residue enables selective removal and subsequent conjugation without triggering unwanted side reactions. This empowers researchers to meticulously design and synthesize peptides with tailored structures suited for diverse therapeutic and research endeavors.

Drug Delivery Systems: Harnessing its exceptional structure, Fmoc-Lys(Pal-Glu-OtBu)-OH contributes to the advancement of sophisticated drug delivery systems. This compound can be seamlessly integrated into peptide-based drug carriers, enhancing solubility, stability, and targeted delivery of pharmaceutical agents. Such innovation elevates therapeutic effectiveness while minimizing adverse effects, ensuring precise drug delivery to designated sites of action.

Bioconjugation: Playing a fundamental role in bioconjugation strategies, Fmoc-Lys(Pal-Glu-OtBu)-OH acts as a vital building block for linking biomolecules like proteins and nucleic acids to diverse functional groups. This versatile capability facilitates the exploration of protein interactions and the development of cutting-edge diagnostic tools. Bioconjugates synthesized with this compound are indispensable for probing intricate biochemical pathways and spearheading the evolution of biosensors.

Immunology Research: In the realm of immunology research, Fmoc-Lys(Pal-Glu-OtBu)-OH emerges as a key player in the synthesis of peptide antigens and the development of vaccines. This compound serves as a cornerstone for constructing peptides that mimic pathogen epitopes, aiding in the meticulous study and elicitation of immune responses. Such a strategic approach is essential for formulating vaccine candidates and unraveling the intricacies of immune mechanisms.

1. Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling

Shuo Zhang, Annamaria Lilienkampf, Mark Bradley Molecules. 2021 Jan 12;26(2):354. doi: 10.3390/molecules26020354.

The cellular plasma membrane plays a fundamental role in biological processes, including cell growth, signaling and transport. The labelling of the plasma membrane with targeted fluorescent probes offers a convenient and non-invasive way to image the morphological changes and dynamics of a membrane in real-time and, despite many examples of fluorescent plasma membrane probes, a "universal targeting/anchoring moiety" is still required. In this study, a small number of stearic acid-based probes labelled with 6-carboxyfluorescein was designed and fabricated via solid-phase synthesis in which variations in both charge and hydrophobicity were explored. To ease the synthesis process, a gram-scale synthesis of the Fmoc-Lys(6-carboxyfluoresein diacetate)-OH building block was developed, allowing the discovery of optimal probes that carried a positively charged amino group and a stearic acid tail that exhibited intense plasma membrane brightness and robust retention.

2. Enhancing the antibacterial effect of chitosan to combat orthopaedic implant-associated infections

Dien Puji Rahayu, Arianna De Mori, Rahmi Yusuf, Roger Draheim, Aikaterini Lalatsa, Marta Roldo Carbohydr Polym. 2022 Aug 1;289:119385. doi: 10.1016/j.carbpol.2022.119385. Epub 2022 Mar 28.

The development of antibacterial resistance imposes the development of novel materials to relieve the burden of infection. Chitosan, a material of natural and sustainable origin, possesses ideal characteristics to translate into a novel biomaterial with antibacterial properties, as it already has these properties and it allows easy and scalable chemical modification to enhance its activity. The aim of the present work was that of producing low molecular weight chitosans that have higher solubility and can remain protonated at physiological pH, thus enhancing the antimicrobial action. This was achieved by reacting acid hydrolysed low molecular weight chitosan with 2-bromoethyleneamine hydrobromide or Fmoc-Lys(Fmoc)-OH to elicit N-(2-ethylamino)-chitosan and N-2(2,6-diaminohexanamide)-chitosan polymers. The latter derivative, CS3H Lys, that was synthesised for the first time, showed superior efficacy against Staphylococcus aureus, supporting further studies for its inclusion in implant coating materials to tackle the burden of orthopaedic implant-associated infections.

3. The use of Fmoc-Lys(Pac)-OH and penicillin G acylase in the preparation of novel semisynthetic insulin analogs

Lenka Záková, Daniel Zyka, Jan Jezek, Ivona Hanclová, Miloslav Sanda, Andrzej M Brzozowski, Jirí Jirácek J Pept Sci. 2007 May;13(5):334-41. doi: 10.1002/psc.847.

In this paper, we present the detailed synthetic protocol and characterization of Fmoc-Lys(Pac)-OH, its use for the preparation of octapeptides H-Gly-Phe-Tyr-N-MePhe-Thr-Lys(Pac)-Pro-Thr-OH and H-Gly-Phe-Phe-His-Thr-Pro-Lys(Pac)-Thr-OH by solid-phase synthesis, trypsin-catalyzed condensation of these octapeptides with desoctapeptide(B23-B30)-insulin, and penicillin G acylase catalyzed cleavage of phenylacetyl (Pac) group from Nepsilon-amino group of lysine to give novel insulin analogs [TyrB25, N-MePheB26,LysB28,ProB29]-insulin and [HisB26]-insulin. These new analogs display 4 and 78% binding affinity respectively to insulin receptor in rat adipose membranes.

GIP (human)

CAT NO. : BAT-006165

Glucagon-like peptide 1 (1-37), human

CAT NO. : BAT-010492