TMSCl works as an acid catalyst precursor for selective esterification of L-aspartic and L-glutamic acids in the presence of primary, secondary and tertiary alcohols. Although excess TMSCl was required for the completion of esterification, the resulting alkyl TMS ether could be azeotropically removed by simple evaporation with alcohol.
ShekarrizM, TaghipoorS, KhaliliAA, JamaraniMS. (2003) Esterification of carboxylic acids with alcohols under microwave irradiation in the presence of zinc triflate. Journal of Chemical Research, 3, 172–173;
5.
PedersenSL, ToftengAP, MalikL, JensenKJ. (2012) Microwave heating in solid-phase peptide synthesis. Chemical Society Reviews, 41, 1826–1844.
6.
HumphreyJM, ChamberlinAR. (1997) Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chemical Reviews, 97, 2243–2266;
7.
HanSY, KimYA. (2004) Recent development of peptide coupling reagents in organic synthesis. Tetrahedron, 60, 2447–2467;
8.
NilssonBL, SoellnerMB, RainesRT. (2005), Chemical Synthesis of Proteins. Annual Review of Biophysics and Biomolecular Structure, 34, 91–118;
9.
ValeurE, BradleyM. (2009) Amide bond formation: beyond the myth of coupling reagents. Chemical Society Reviews, 38, 606–631.
10.
BelshawPJ, MzengezaS, LajoieGA. (1990) Chlorotrimethylsilane mediated formation of omega-allyl esters of aspartic and glutamic acids. Synthetic Communications, 20, 3157–3160;
11.
BrookMA, ChanTH. (1983) A simple procedure for the esterification of carboxylic acids. Synthesis, 1983, 201–203;
12.
IzumiM, FukaseK, KusumotoS. (2002) TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycbside for anomeric protection. Bioscience Biotechnology Biochemistry, 66, 211–214;
13.
LiJ, ShaY. (2008) A convenient synthesis of amino acid methyl esters. Molecules, 13, 1111–1119.
14.
RamalingamK, WoodardRW. (1988) Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones. The Journal of Organic Chemistry, 53, 1900–1903.
15.
FukaseY, FukaseK, KusumotoS. (1999) Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions. Tetrahedron Letters, 40, 1169–1170;
16.
RamapanickerR, GuptaR, MeghaR, ChandrasekaranS. (2011) Applications of propargyl esters of amino acids in solution-phase peptide synthesis. International Journal of Peptides, 2011, 1–10.
