146982-27-6

Basic information

• Product Name: FMOC-LYS(ALOC)-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-EPSILON-ALLYL-OXYCARBONYL-L-LYSINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-EPSILON-ALLYLOXYCARBONYL-L-LYSINE;N-ALPHA-FMOC-N-EPSILON-ALLYLOXYCARBONYL-L-LYSINE;N-ALPHA-FMOC-N-EPSILON-ALLOC-L-LYSINE;FMOC-LYS(ALLOC)-OH;FMOC-LYS(ALOC)-OH;FMOC-LYSINE(ALOC)-OH;FMOC-L-LYS(ALLOC)-OH
• CAS NO: 146982-27-6
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.5
• Product Categories: Amino Acids;Lysine [Lys, K];Fmoc-Amino Acids and Derivatives;peptides
• Mol File: 146982-27-6.mol

Chemical Properties

• Melting Point: 87-91℃
• Boiling Point: 689.699 ºC at 760 mmHg
• Flash Point: 370.917 ºC
• Appearance: /Solid
• Density: 1.237 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• PKA: 3.88±0.21(Predicted)
• BRN: 5893081
• CAS DataBase Reference: FMOC-LYS(ALOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-LYS(ALOC)-OH(146982-27-6)
• EPA Substance Registry System: FMOC-LYS(ALOC)-OH(146982-27-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 146982-27-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C25H28N2O6/c1-2-15-32-24(30)26-14-8-7-13-22(23(28)29)27-25(31)33-16-21-19-11-5-3-9-17(19)18-10-4-6-12-20(18)21/h2-6,9-12,21-22H,1,7-8,13-16H2,(H,26,30)(H,27,31)(H,28,29)/t22-/m0/s1

Upstream product

• 105047-45-8 Fmoc-Lys-OH 
• 2937-50-0 Allyl chloroformate 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 147529-99-5 N^Ε-allyloxycarbonyl-L-lysine hydrochloride 

Downstream Products

• 1433682-14-4 C₄₉H₆₁N₁₁O₅ 
• 1433682-06-4 C₄₇H₅₈N₁₀O₄ 
• 1433682-10-0 C₄₇H₅₈N₁₀O₅ 
• 1387556-15-1 C₄₀H₄₇N₇O₁₂ 
• 1608473-83-1 Fmoc-Ile-Glu-Pro-Lys(Alloc)-Tyr-Arg-Leu-Arg-Tyr-CONH₂ 
• 1443329-22-3 H-Lys-c[Lys-Nle-Aib-Val-Glu]-Lys-Tyr-NH₂ 
• 1426413-17-3 C₇₂H₁₀₇N₁₅O₁₈S 
• 1423138-53-7 Ac-Glu-Val-Val-Lys-Phe-Met(O₂)-c(NH-CO)^7-11[Glu-Val-Tyr-Gln-Lys]-Ser-Tyr-NH₂ 
• 1423138-52-6 Ac-Glu-Val-Val-Lys-Phe-Met(O₂)-Glu-Val-Tyr-Gln-Lys-Ser-Tyr-NH₂ 
• 1423138-50-4 Ac-Glu-Val-Glu-Lys-Phe-Met(O₂)-Lys-Val-Tyr-Gln-Arg-Ser-Tyr-NH₂ 
• 1423138-51-5 Ac-Glu-Val-c(NH-CO)^3-7[Glu-Lys-Phe-Met(O₂)-Lys]-Val-Tyr-Gln-Arg-Ser-Tyr-NH₂ 

Relevant articles and documents

A procedure for the large scale preparation of N(ε)-Alloc-lysine and N(ε)-Alloc-N(α)-Fmoc-lysine

This report describes a convenient procedure for a 100 g scale preparation of Fmoc-Lys(Alloc) in 85% yield. This method can be easily adapted to a near one-pot procedure with slightly reduced yields. Without requiring the isolation of the intermediate Lys(Alloc).

Cyclization of peptides through a urea bond: Application to the Arg-Gly-Asp tripeptide

Various synthetic cyclopeptides bind different cellular proteins with high affinity and specificity. In this study, we designed a new series of cyclic tetrapeptides containing the RGD sequence, a ligand for the α vβ3 integrin receptor, in which the ring closure was performed through a urea bond between the a-amino group of the peptide and either the α- or the ε-amino group of an additional lysine. Interestingly, we showed that the urea-closed peptide had a higher affinity for αvβ3 receptors than a reference pentacyclopeptide. Moreover, the synthetic strategy allows coupling of the resulting cyclic tetrapeptide through the carboxylic acid moiety of its lysine residue to fluorescent molecules or drugs. In addition, this strategy could be easily adapted for the cyclization of any other peptides.

New effector conjugates, process for their production and their pharmaceutical use

Conjugates of epothilones and epothilone derivatives (as effectors) with suitable biomolecules (as recognition units) are described. Their production is carried out by the effectors being reacted with suitable linkers, and the compounds that are produced are conjugated to the recognition units. The pharmaceutical use of conjugates for treating proliferative or angiogenesis-associated processes is described.

Allyl side chain protection in peptide synthesis

A system for the protection of amino acid side-chain functional moieties during peptide synthesis, comprising the use of allyl protecting groups, such as, for example, allyl ether, allyl ester, allyl thioether allyloxycarbonyl and allyloxymethyl groups. The present allyl protecting groups do not exert adverse steric effects on peptide bond condensation, and are fully orthogonal to a variety of popular αN-protecting groups, including Fmoc and tBoc. Moreover, allyl deprotection is mild, and does not result in the formation of reactive carbonium ions. Allyl side-chain protection can be used alone or in conjunction with other types of side-chain protecting groups.