Fmoc-Lys(N3)-OH

Fmoc-Lys(N3)-OH Property

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

HS Code 

2929900090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H228Flammable solid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

Fmoc-Lys(N3)-OH Chemical Properties,Usage,Production

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