127656-85-3Relevant articles and documents
Building blocks for glycopeptide synthesis: Glycosylation of 3-Mercaptopropionic acid and Fmoc amino acids with unprotected carboxyl groups
Elofsson,Walse,Kihlberg
, p. 7613 - 7616 (1991)
3-Mercaptopropionic acid and Fmoc amino acids, having unprotected carboxyl groups, were glycosylated with sugar 1,2-trans-acetates in 90 and 53-65% yields, respectively, under lewis acid promotion. The synthesis of a neoglycopeptide illustrates the use of the building blocks in solid phase peptide synthesis.
Oxytocin analogues with O-glycosylated serine and threonine in position 4
Marcinkowska,Borovickova,Slaninova,Grzonka
, p. 1335 - 1344 (2008/09/19)
Oxytocin structure was modified in position 4 using glycoamino acids. Procedure for transformation of Fmoc-protected serine and threonine derivatives into appropriate O-glycosylated precursors suitable for solid phase peptide synthesis (SPPS) was worked o
Preparation of Building Blocks for Glycopeptide Synthesis by Glycosylation of Fmoc Amino Acids Having Unprotected Carboxyl Groups
Salvador, Lourdes A.,Eloffson, Mikael,Kihlberg, Jan
, p. 5643 - 5656 (2007/10/02)
Nα-Fmoc amino acids with an unprotected α-carboxyl group have been glycosylated with carbohydrate 1,2-trans peracetates using Lewis acids as promoters.Aliphatic and phenolic O- and S-glycosides of amino acids, with a 1,2-trans anomeric configuration, were obtained as products in 34-65percent yields.The glycosylated building blocks have the protective groups of choice (i.e.O-acetyl and Nα-Fmoc) for direct use in stepwise synthesis of glycopeptides.The starting materials are readily available and the method does not require an extensive experience in synthetic carbohydrate chemistry.