6298-03-9

Basic information

• Product Name: H-LYS(ALLOC)-OH
• Synonyms: nδ-alloc-l-lysine;(S)-6-(((Allyloxy)carbonyl)aMino)-2-aMinohexanoic acid;NSC 45852;(2S)-2-Amino-6-[[(prop-2-en-1-yloxy)carbonyl]amino]hexanoic acid;N6-[(2-Propen-1-yloxy)carbonyl]-L-lysine;L-Lys(Aloc)-OH;Ne-Allyloxycarbonyl-L-lysine;(2S)-2-amino-6-(prop-2-enoxycarbonylamino)hexanoic acid
• CAS NO: 6298-03-9
• Molecular Formula: C₁₀H₁₈N₂O₄
• Molecular Weight: 230.26092
• Mol File: 6298-03-9.mol

Chemical Properties

• Boiling Point: 414.9°C at 760 mmHg
• Flash Point: 204.7°C
• Appearance: /
• Density: 1.153g/cm³
• Vapor Pressure: 4.8E-08mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: Store at RT.
• PKA: 2.53±0.24(Predicted)
• CAS DataBase Reference: H-LYS(ALLOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-LYS(ALLOC)-OH(6298-03-9)
• EPA Substance Registry System: H-LYS(ALLOC)-OH(6298-03-9)

Safety Data

• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 6298-03-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
H-LYS(ALLOC)-OH is used as a protected amino acid in chemical synthesis for the preparation of complex organic molecules and pharmaceutical compounds. The alloc group provides selective protection, allowing chemists to control the reactivity of the molecule and avoid unwanted side reactions.
Used in Drug Development:
H-LYS(ALLOC)-OH is used as a building block in the development of new drugs, particularly in the synthesis of peptide-based therapeutics. The protected L-lysine derivative can be incorporated into peptide sequences, and the alloc group can be selectively removed when needed, enabling the formation of desired peptide bonds and the synthesis of bioactive peptides.
Used in Peptide Synthesis:
H-LYS(ALLOC)-OH is used as a protected amino acid in solid-phase peptide synthesis (SPPS) for the stepwise assembly of peptide chains. The alloc group allows for the controlled addition of amino acids to the growing peptide chain, and its selective removal enables the formation of peptide bonds without affecting other functional groups in the molecule.
Used in Bioconjugation:
H-LYS(ALLOC)-OH is used as a reactive handle in bioconjugation for the attachment of various functional groups, such as fluorescent dyes, affinity tags, or other biomolecules, to peptides or proteins. The alloc group can be selectively removed under mild conditions, allowing for the introduction of the desired functional group without disrupting the integrity of the biomolecule.
Used in Proteomics and Peptide Microarrays:
H-LYS(ALLOC)-OH is used as a building block in the synthesis of peptides for proteomics studies and peptide microarrays. The protected L-lysine derivative enables the generation of diverse peptide sequences, facilitating the investigation of protein-protein interactions, enzyme substrate specificity, and other biological processes.

InChI:InChI=1/C10H18N2O4/c1-2-7-16-10(15)12-6-4-3-5-8(11)9(13)14/h2,8H,1,3-7,11H2,(H,12,15)(H,13,14)

Upstream product

• 104669-73-0 N^α-(tert-butoxycarbonyl)-N^ε-(allyloxycarbonyl)-L-lysine 
• 56-87-1 L-lysine 
• 2937-50-0 Allyl chloroformate 
• 372-75-8 Citrulline 

Downstream Products

• 159857-88-2 N-Cbz-Phe-Lys(ε-Alloc)OH 
• 1279111-08-8 Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine 
• 1279111-09-9 Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-4-fluorodeacetylcolchicine 
• 1279111-12-4 C₅₅H₆₀FN₅O₁₃ 
• 1279111-11-3 C₅₅H₆₁N₅O₁₃ 
• 71448-16-3 Cbz-L-Phe-L-Lys-OH 
• 159857-89-3 N-Cbz-Phe-Lys(ε-Alloc)-4-aminobenzyl alcohol 
• 159857-90-6 N-Cbz-Phe-Lys(ε-Alloc)-4-aminobenzyl 4-nitrophenyl carbonate 
• 1160844-44-9 C₃₈H₄₅N₅O₁₁ 
• 1160844-43-8 C₃₁H₄₂N₄O₇ 

Relevant articles and documents

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.

Design, synthesis, and antitumor activity of 4-halocolchicines and their pro-drugs activated by cathepsin B

Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.

PALLADIUM-CATALYZED REACTION OF TRIBUTYLTIN HYDRIDE. SELECTIVE AND VERY MILD DEPROTECTION OF ALLYL AND ALLYLOXYCARBONYL DERIVATIVES OF AMINO-ACIDS.

Allyl(All) and Allyloxycarbonyl(Alloc) amino-acid derivatives are deprotected through palladium-catalyzed hydrostannolysis by Bu3SnH in a highly selective manner.Benzyl and benzyloxycarbonyl groups are stable under these conditions.Moreover the allyl and Alloc groups seem orthogonal to the t-butyl and t-butoxycarbonyl protecting groups.