Fmoc-Lys(N3)-OH Chemical Properties

Melting point:

78 °C(dec.)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

color 

White to Almost white

InChIKey

PJRFTUILPGJJIO-DETXXQSHNA-N

SMILES

C(C1C2=CC=CC=C2C2=CC=CC=C12)OC(=O)N[C@H](C(=O)O)CCCCN=[N+]=[N-] |&1:18,r|

Safety Information

HS Code 

2929900090

Fmoc-Lys(N3)-OH Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

The side chain azido (N3) group is stable in trifluoroacetic acid or piperidine. It can be readily converted to amine and to synthesis side chain modified peptides and proteins by Solid Phase Peptide Synthesis (SPPS) methodology.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-aminohexanoic acid (Fmoc-lysine, 2.03 g, 5.51 mmol) was used as a starting material, which was co-dissolved in methanol (70 mL) with CuSO4 (88 mg, 0.35 mmol) and K2CO3 (2.46 g, 17.83 mmol). Subsequently, imidazole-1-sulfonyl azide hydrochloride (3,1.40 g, 6.70 mmol) was added in batches and the resulting suspension was stirred overnight at room temperature. Upon completion of the reaction, the solvent was removed by vacuum evaporation and the residue was redissolved in dichloromethane (50 mL). The resulting solution was washed with 1 M aqueous hydrochloric acid (50 mL) and the aqueous phase was re-extracted with dichloromethane (3 x 50 mL). The organic phases were combined and the crude product was purified by gradient column chromatography (eluent ratio: dichloromethane/methanol/acetic acid, 96.5%/3%/0.5% → 93.5%/6%/0.5%). The purified product was lyophilized from dioxane to give a colorless oil (1.94 g, 89% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and HRMS (ESI+): 1H-NMR δ 7.76 (d, J = 7.5 Hz, 2H), 7.59 (d, J = 6.9 Hz, 2H), 7.40 (t, J = 7.5 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 5.34 (d, J = 7.8 Hz, 1H), 4.54 (br s, 1H), 4.43 (d, J = 6.6 Hz, 2H), 4.22 (t, J = 6.6 Hz, 1H), 3.27 (t, J = 6.6 Hz, 2H), 1.3-2.0 (m, 2H); HRMS (ESI+) m/z calcd for C21H23N4O4 [M + H ]+ 395.1719, found 395.1718.

References

[1] European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 1117 - 1129
[2] Chemical Communications, 2011, vol. 47, # 9, p. 2589 - 2591
[3] Chemical Communications, 2018, vol. 54, # 23, p. 2846 - 2849
[4] Patent: EP2532639, 2012, A1. Location in patent: Page/Page column 5; 6
[5] Angewandte Chemie, International Edition, 2015, vol. 54, # 19, p. 5784 - 5788

Fmoc-Lys(N3)-OH(159610-89-6)Related Product Information

• (s)-3-(fmoc-amino)-n-trityl-adipic acid 6-amide
• Fmoc-D-Lys(ipr,Boc)-OH
• FMOC-LYS(MCA)-OH
• FMOC-LYS(ALOC)-OH
• Fmoc-Lys(nicotinoyl)-OH
• FMOC-LYS(5-FAM)-OH
• Fmoc-HoLys(N3)-OH
• Fmoc-Lys(Ddiv)-OH
• FMOC-LYS(FMOC)-OH
• FMoc-Lys-AMC.HCl
• FMOC-L-LYS(DANSYL)-OH
• FMoc-Aea-OH
• N(ALPHA)-FMOC-N(EPSILON)-DABCYL-L-LYSINE
• FMOC-LYS(BOC)(ME)-OH
• FMOC-LYS(ME)2-OH HCL
• FMOC-LYS(DNP)-OH
• Fmoc-Lys(Trt)-OH
• FMOC-LYS(ME3)-OH HCL