The Journal of organic chemistry

A concise β-lactam route to short peptide segments containing β, β-disubstituted β-amino acids

C Palomo, M Oiarbide, S Bindi

Index: Palomo, Claudio; Oiarbide, Mikel; Bindi, Simona Journal of Organic Chemistry, 1998 , vol. 63, # 8 p. 2469 - 2474

Full Text: HTML

Citation Number: 34

Abstract

An efficient epimerization-free route toward β, β-disubstituted β-amino acid-containing peptides is described. The methodology involves the use of 4, 4-disubstituted-N-Boc β- lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the β- ...

Related Articles:

Acyl and sulfonyl isocyanates in. beta.-lactam synthesis

[Barrett, Anthony G. M.; Betts, Michael J.; Fenwick, Ashley Journal of Organic Chemistry, 1985 , vol. 50, # 2 p. 169 - 175]

2, 2, 2-Trichloroethylsulphonyl, 2, 2, 2-trichloroethoxysulphonyl, and trifluoroacetyl isocyanates in β-lactam synthesis

[Barrett, Anthony G. M.; Fenwick, Ashley; Betts, Michael J. Journal of the Chemical Society, Chemical Communications, 1983 , # 6 p. 299 - 301]

Acyl and sulfonyl isocyanates in. beta.-lactam synthesis

[Barrett, Anthony G. M.; Betts, Michael J.; Fenwick, Ashley Journal of Organic Chemistry, 1985 , vol. 50, # 2 p. 169 - 175]

Acyl and sulfonyl isocyanates in. beta.-lactam synthesis

[Barrett, Anthony G. M.; Betts, Michael J.; Fenwick, Ashley Journal of Organic Chemistry, 1985 , vol. 50, # 2 p. 169 - 175]

Novel 5-Hydroxytryptamine 4 (5-HT4) Receptor Agonists. Synthesis and Gastroprokinetic Activity of 4-Amino-N (2-(1-aminocycloalkan-1-yl) ethyl)-5-chloro-2 …

[Suzuki, Takeshi; Imanishi, Naoki; Itahana, Hirotsune; Watanuki, Susumu; Miyata, Keiji; Ohta, Mitsuaki; Nakahara, Hideaki; Yamagiwa, Yoko; Mase, Toshiyasu Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 7 p. 1116 - 1124]

More Articles...