1202003-49-3 Usage
Description
FMoc-α-Me-Lys(Boc)-OH, also known as (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid, is a specialty chemical compound used in the synthesis of peptides and proteins. It is a protected amino acid derivative, featuring a 9-fluorenylmethoxycarbonyl (Fmoc) group for the α-amino protection and a tert-butyloxycarbonyl (Boc) group for the side chain protection. The presence of a methyl group on the α-carbon and the specific stereochemistry at the α-carbon center (S-configuration) make it a unique building block for the development of peptide-based therapeutics and analogs.
Uses
Used in Pharmaceutical Industry:
FMoc-α-Me-Lys(Boc)-OH is used as a reagent for the synthesis of peptide analogs containing (S)-α-methyl-lysine for the development of novel therapeutic agents.
Used in Research Applications:
FMoc-α-Me-Lys(Boc)-OH is used as a reagent in the preparation and biological evaluation of vapreotide analogs containing (S)-α-methyl-lysine, which can help in understanding the structure-activity relationships and potential applications of these analogs in various biological processes and diseases.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1202003-49-3 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,0,2,0,0 and 3 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1202003-49:
(9*1)+(8*2)+(7*0)+(6*2)+(5*0)+(4*0)+(3*3)+(2*4)+(1*9)=63
63 % 10 = 3
So 1202003-49-3 is a valid CAS Registry Number.
1202003-49-3Relevant articles and documents
Novel synthesis of various orthogonally protected Cα- methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine
Banerjee, Souvik,Wiggins, Walker J.,Geoghegan, Jessie L.,Anthony, Catherine T.,Woltering, Eugene A.,Masterson, Douglas S.
, p. 6307 - 6319 (2013/09/23)
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
Chauhan, Satendra S.
scheme or table, p. 6913 - 6915 (2010/05/18)
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,