N-alpha-FMOC-Nepsilon-BOC-L-Lysine

Base Information

• Chemical Name: N-alpha-FMOC-Nepsilon-BOC-L-Lysine
• CAS No.: 71989-26-9
• Molecular Formula: C26H32N2O6
• Molecular Weight: 468.55
• Hs Code.: 29224999
• NSC Number: 334302
• DSSTox Substance ID: DTXSID30868059
• Mol file: 71989-26-9.mol

Synonyms:2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(tert-butoxycarbonylamino)hexanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(tert-butoxycarbonylamino)hexanoate;N6-(tert-Butoxycarbonyl)-N2-((9H-fluoren-9-ylmethoxy)carbonyl)-L-lysine;N-alpha-FMOC-Nepsilon-BOC-L-Lysine;Fmoc-L-Lys(Boc)-OH;Fmoc-Lys(Boc);Fmoc-L-Lys(Boc);N-α-Fmoc-N-ε-Boc-L-lysine;Fmoc-Lys(Boc)-OH;N-alpha-FMOC-Nepsilon-BOC-L-Lysine;Nalpha-(9-Fluorenylmethoxycarbonyl)-nepsilon-(tert-butoxycarbonyl)-L-lysine;N6-(tert-butoxycarbonyl)-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine;N-alpha-Fmoc-N-epsilon-Boc-L-lysine;Fmoc-Lys(Boc)-OH;

Chemical Property of N-alpha-FMOC-Nepsilon-BOC-L-Lysine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 130-135 °C (dec.)
• Refractive Index: -12 ° (C=1, DMF)
• Boiling Point: 685.7 °C at 760 mmHg
• PKA: 3.88±0.21(Predicted)
• Flash Point: 368.5 °C
• PSA: 113.96000
• Density: 1.21 g/cm³
• LogP: 5.45510
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 468.22603674
• Heavy Atom Count: 34
• Complexity: 684

Purity/Quality:

99% ^*data from raw suppliers

N-alpha-Fmoc-Nε-Boc-D-lysine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• 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. 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.

Technology Process of N-alpha-FMOC-Nepsilon-BOC-L-Lysine

There total 14 articles about N-alpha-FMOC-Nepsilon-BOC-L-Lysine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 88.0%

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + H-Lys(Boc)-OH (2418-95-3) → Fmoc-Lys(Boc)-OH (71989-26-9)

Guidance literature:

With triethylamine; In water; acetonitrile; for 1h;

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Copper(II); (S)-2-amino-6-tert-butoxycarbonylamino-hexanoate → Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9)

Guidance literature:

Copper(II); (S)-2-amino-6-tert-butoxycarbonylamino-hexanoate; With 8-quinolinol; sodium hydrogencarbonate; sodium carbonate; In water; at 20 ℃; for 4h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In water; at 20 ℃; for 2h;

upstream raw materials:

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

di-tert-butyl dicarbonate

L-Lysine hydrochloride

Downstream raw materials:

Fmoc-Lys(Boc)-ONp

Fmoc-Lys(Boc)-OTDO

carbon dioxide

(S)-8-tert-Butoxycarbonylamino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-octanoic acid 4-nitro-benzyl ester

Refernces

• 1、 -. "PROPYL CATIONIC PEPTIDE LIPIDS, SYNTHESIS METHOD THEREOF, AND APPLICATION THEREOF". Paragraph 0077; 0087. . Retrieved 2018/01/13.
• 2、 Ankner, Tobias,Norberg, Thomas,Kihlberg, Jan. "Mild oxidative cleavage of 9-BBN-protected amino acid derivatives". . p. 3767 - 3770. Retrieved 2015/06/16.