157886-31-2Relevant academic research and scientific papers
Efficient synthesis of differentially protected (S,S)-2,7- diaminooctanedioic acid, the dicarba analogue of cystine
Lange, Meinolf,Fischer, Peter M.
, p. 2053 - 2061 (2007/10/03)
Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carb
A detailed investigation of the preparation of 2,7-diaminosuberic acid and 2,5-diaminoadipic acid derivatives using Kolbe electrolysis
Hiebl, Johann,Blanka, Michael,Guttman, Andras,Kollmann, Hermann,Leitner, Kornelia,Mayrhofer, Guenter,Rovenszky, Franz,Winkler, Karin
, p. 2059 - 2074 (2007/10/03)
The yield of protected 2,7-diaminosuberic acid (DAS) prepared by Kolbe reaction of N-protected α-glutamic acid esters is dependent on solvent, temperature, concentration of carboxylate onion, and protecting groups. The highest yield of protected L,L-2,7-diaminosuberic acid is obtained with Boc-Glu-OMe as starting material using MeOH/pyridine/NaOMe as electrolyte.
Solution synthesis of a dimeric pentapeptide: Diketopiperazine cyclisation of Glu-Asp dipeptide esters and Asp-racemisation during segment condensation
Fischer,Solbakken,Undheim
, p. 2277 - 2288 (2007/10/02)
A haemoregulatory peptide analogue derived from the cystine-dimerised pentapeptide Glp-Glu-Asp-Cys-Lys-OH, in which the cystine residue has been replaced by an isosteric L,L-2,7-diaminosuberic acid moiety, was prepared by segment condensation in solution.
Useful Intermediates for Synthesis of Dicarba Analogues of Cystine Peptides: Selectively Protected α-Aminosuberic Acid and α,α'-Diaminosuberic Acid of Defined Stereochemistry
Nutt, Ruth F.,Strachan, Robert G.,Veber, Daniel F.,Holly, Frederick W.
, p. 3078 - 3080 (2007/10/02)
Practical procedures are described for synthesis of selectively protected α-aminosuberic acid and α,α'-diaminosuberic acid by the mixed Kolbe electrolytic decarboxylative dimerization of two different carboxylic acids.Stereochemistry is established by the choice of L- or D-glutamic acid precursors.The method is illustrated by the synthesis of α-tert-butyl Nα-Boc-Nα'-Cbz-LL-α,α'-diaminosuberate (6) and α-tert-butyl ω-methyl Nα-Boc-D-α-aminosuberate (10) which can be used directly in the preparation of dicarba and desaminodicarba analogues of cystinepeptides.Although statistically controlled mixtures are produced, facile procedures for isolation of the products have been worked out.No racemization of chiral centers was detected.
