1202003-49-3

Basic information

• Product Name: FMoc-α-Me-Lys(Boc)-OH
• Synonyms: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid;N6-[(1,1-Dimethylethoxy)carbonyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-lysine;(S)-N-ALPHA-FMOC-N-EPSILON-BOC-ALPHA-METHYLLYSINE;(S)-Na-Fmoc-NW-Boc-α-Methyllysine;Fmoc-alpha-Me-L-Lys(Boc)-OH;(2S)-6-{[(tert-butoxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylhexanoic acid;(9H-Fluoren-9-yl)MethOxy]Carbonyl Alpha-Methyl-Lys(Boc)-OH;N6-Boc-N2-Fmoc-alfa-Me--L-Lys-OH
• CAS NO: 1202003-49-3
• Molecular Formula: C₂₇H₃₄N₂O₆
• Molecular Weight: 482.56866
• Product Categories: α-Methyl Amino Acids
• Mol File: 1202003-49-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 687.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.196±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.92±0.41(Predicted)
• CAS DataBase Reference: FMoc-α-Me-Lys(Boc)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMoc-α-Me-Lys(Boc)-OH(1202003-49-3)
• EPA Substance Registry System: FMoc-α-Me-Lys(Boc)-OH(1202003-49-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-40-67
• Safety Statements: 23-24/25-36/37
• TSCA: No
• Hazardous Substances Data: 1202003-49-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1202003-49-3 differently. You can refer to the following data:
1. (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid is a reagent in the preparation/biological evaluation of a vapreotide analogs containing (S)?-?α-?methyl-?lysine.
2. (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid is a reagent in the preparation/biological evaluation of a vapreotide analogs containing (S)-α-methyl-lysine.

Synthesis

Benzyl (2R,3S)-(?)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-α-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-α-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-α-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1202003-48-2 (L)-Fmoc-α-Me-Lys-OH 
• 1202003-44-8 (L)-α-Me-Lys(Boc)-OH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 1453178-51-2 fluorenylmethyloxycarbonylamino-2-methylhexanoic acid hydrochloride 
• 1453178-49-8 (9H-fluoren-9-yl)methyl (S)-2-(ethoxycarbonyl)-6-(1,3-dioxoisoindolin-2-yl)hexan-2-ylcarbamate 
• 1453179-18-4 (R)-2-(N-butylphthalimido)-3-ethoxy-2-methyl-3-oxopropanoic acid 
• 17377-68-3 Diethyl 2-(N-butylphthalimido)-2-methylmalonate 

Relevant articles and documents

Novel synthesis of various orthogonally protected Cα- methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine

Prochiral malonic diesters containing a quaternary carbon center have been successfully transformed into a diverse set of tBoc-Fmoc- α2,2-methyllysine-OH analogues through chiral malonic half-ester intermediates obtained via enzymatic (Pig Liver Esterase, PLE) hydrolysis. The variety of chiral half-ester intermediates, which vary from 1 to 6 methylene units in the side chain, are achieved in moderate to high optical purity and in good yields. The PLE hydrolysis of malonic diesters with various side chain lengths appears to obey the Jones's PLE model according to the stereochemical configurations of the resulting chiral half-esters. The established synthetic strategy allows the construction of both enantiomers of α2,2-methyllysine analogues, and a (S)-β2,2- methyllysine analogue from a common synthon by straightforward manipulation of protecting groups. Two different straightforward and cost effective synthetic strategies are described for the synthesis of α2,2-methyllysine analogues. The described strategies should find significant usefulness in preparing novel peptide libraries with unnatural lysine analogues. A Vapreotide analogue incorporating (S)-α2,2-methyllysine was prepared. However, the Vapreotide analogue with (S)-α-methyl-α-lysine is found to lose its specific binding to somatostatin receptor subtype 2 (SSTR2).

Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide,