N-Boc-N'-Cbz-L-lysine Chemical Properties

Melting point:

75.0 to 79.0 °C

Boiling point:

587.0±50.0 °C(Predicted)

Density 

1.176±0.06 g/cm3(Predicted)

refractive index 

-8 ° (C=2.5, AcOH)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

almost transparency in Acetic acid

form 

powder to crystal

pka

3.99±0.21(Predicted)

color 

White to Almost white

BRN 

1917222

InChI

InChI=1S/C19H28N2O6/c1-19(2,3)27-18(25)21-15(16(22)23)11-7-8-12-20-17(24)26-13-14-9-5-4-6-10-14/h4-6,9-10,15H,7-8,11-13H2,1-3H3,(H,20,24)(H,21,25)(H,22,23)/t15-/m0/s1

InChIKey

BDHUTRNYBGWPBL-HNNXBMFYSA-N

SMILES

C(O)(=O)[C@H](CCCCNC(OCC1=CC=CC=C1)=O)NC(OC(C)(C)C)=O

CAS DataBase Reference

2389-45-9(CAS DataBase Reference)

EPA Substance Registry System

N2-tert-Butoxycarbonyl-N6-benzyloxycarbonyl lysine (2389-45-9)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

2924 29 70

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-N'-Cbz-L-lysine Usage And Synthesis

Uses

Boc-Lys(Z)-OH, is used in the synthesis of Isodesmosine Chloride (I815050), which is a component of elastin.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of N-Boc-N'-Cbz-L-lysine from N-alpha-Boc-L-lysine and phenylmethoxycarbonylsuccinimide was as follows: to a mixed solution of (2S)-6-amino-2-(tert-butoxycarbonylamino)hexanoic acid (100.00 g, 406.01 mmol, 1.00 equiv) and NaHCO3 (102.33 g 1.22 mol, 3.00 eq.) in a mixed solution of THF (1000 mL) and water (1000 mL) was slowly added CbzOSu (101.19 g, 406.01 mmol, 1.00 eq.) at 0 °C. Subsequently, the reaction mixture was stirred at 30 °C for 16 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5-6 with 1N HCl and then extracted with ethyl acetate (600 mL x 3). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product (2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (142.00 g, 373.26 mmol, 91.9% yield) as a yellow oil.

References

[1] Patent: US2016/96830, 2016, A1. Location in patent: Paragraph 0368-0369

N-Boc-N'-Cbz-L-lysine(2389-45-9)Related Product Information

• Iminodibenzyl
• Poly-L-lysine
• 6-Aminocaproic acid
• N-Carbobenzyloxyglycine
• tert-Butyl carbazate
• L-Lysine
• Hexanoic acid
• Poly(L-lysine hydrobromide)
• N-Boc-N'-Fmoc-D-lysine
• N-Boc-N'-Fmoc-L-Lysine
• Boc-His(Trt)-OH
• N-alpha-t-Butyloxycarbonyl-N-epsilon-benzyloxycarbonyl-L-lysinol
• Boc-D-Ser(Bzl)-OH
• N-BOC-O-Benzyl-L-serine
• BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER
• N-BOC-L-Prolinal
• N-Boc-D-alaninol
• N-Boc-D-Phenylalaninol