Fmoc-Lys(Boc)-OH Chemical Properties

Melting point:

130-135 °C (dec.)

alpha 

-12 º (c=2,DMF 24 ºC)

Boiling point:

570.69°C (rough estimate)

Density 

1.2301 (rough estimate)

refractive index 

-12 ° (C=1, DMF)

storage temp. 

Store below +30°C.

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.88±0.21(Predicted)

form 

Powder

color 

White

optical activity

[α]20/D 12±1°, c = 1% in DMF

Water Solubility 

Slightly soluble in water.

BRN 

4217767

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

UMRUUWFGLGNQLI-QFIPXVFZSA-N

CAS DataBase Reference

71989-26-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25-36/37/39-27-26

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:N-alpha-FMOC-Nepsilon-BOC-L-Lysine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Fmoc-Lys(Boc)-OH Usage And Synthesis

Description

Fmoc-Lys(Boc)-OH (Na-Fmoc-Ne-Boc-L-lysine) has emerged as the standard Fmoc-Lys derivative used in peptide synthesis. The Boc group on the side chain is stable under basic conditions and remains in place even through many Fmoc deprotection cycles. The Boc group of Fmoc-Lys(Boc)-OH is readily removed with trifluoroacetic acid (TFA) during cleavage of the peptide product from Wang resin or Rink amide resin. It could self-assemble to sphere like morphology in all conditions irrespective of concentration and heating. To prepare the FAPI-04 dimer complex, this compound could used as a linker to conjugate two FAPI-04 structures by an amide reaction. After further modification, the product can perform cancer theranostics[1-2].

Chemical Properties

white to light yellow crystal powde

Uses

It is used to prepare dimeric RGD peptide-paclitaxel conjugate as model for integrin-targeted drug delivery. It is also used to synthesize DOTA-conjugated multivalent cyclic-RGD peptide dendrimers for tumor targeting and imaging use.

Uses

Fmoc-Lys(Boc)-OH can be used for:

• The solid-phase synthesis of pentasubstituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts by coupling with p-methylbenzhydrylamine (MBHA) resin.
• Fmoc-based peptide synthesis of bis-naphthalene diimide, a threading intercalator.
• Synthesis of ε-Boc-ε-(3,5-bis-trifluoromethyl-benzyl)-α-Fmoc-L-Lysine to be used as ¹⁹F NMR based screening tool.

References

[1] Gour N, et al. Controlled aggregation properties of modified single amino acids. ChemRxiv, 2021; 46.
[2] Zhong X, et al. Synthesis and Preclinical Evaluation of a Novel FAPI-04 Dimer for Cancer Theranostics. Molecular Pharmaceutics, 2023; 20: 2402–2414.

Fmoc-Lys(Boc)-OH(71989-26-9)Related Product Information

• Fmoc-Aib-OH
• 9-Fluorenylmethyl chloroformate
• N-(9-Fluorenylmethoxycarbonyloxy)succinimide
• L-Lysine
• AC-HIS-OH H2O
• Cbz-beta-Amino-L-alanine
• DI-TERT-BUTYL ETHER
• FMOC-Ala-OH
• FMOC-S-trityl-L-cysteine
• Fmoc-Asp(OtBu)-OH
• FMOC-L-Valine
• FMOC-L-Methionine
• FMOC-N-METHYL-TRANEXAMIC ACID
• Fmoc-L-Tyr(propargyl)-OH
• Fmoc-Gly-OH
• FMOC-O-tert-Butyl-L-serine
• Fmoc-Asn(Trt)-OH
• FMOC-TRANEXAMIC ACID