0000000000174513
AUTHOR
Peter Braun
Effects of glycosylation on fragments of tumour associated human epithelial mucin MUC1.
The glycodecapeptide AcPAPGS(alpha GalNAc)T(alpha GalNAc)APPA and the C-terminal glycohexapeptide AcS(alpha GalNAc)T(alpha GalNAc)APPA have been synthesized by applying the N-terminal Fmoc group in combination with the heptyl ester cleavable by lipase-catalyzed hydrolysis at pH 7. The solution conformation of these MUC1-related synthetic glycopeptides and the control, non-glycosylated decapeptide AcPAPGSTAPPA have been investigated using NMR spectroscopy. The structural studies indicate that the glycohexapeptide has a folded structure in solution. For this molecule, unrestrained molecular dynamics has been used to confirm the presence of the observed solution through-space connections. The …
Chemoselective Removal of Protecting Groups from O-Glycosyl Amino Acid and Peptide (Methoxyethoxy)ethyl Esters Using Lipases and Papain
The selective C-terminal deprotection of O-glycopeptide (methoxyethoxy)ethyl esters is achieved under mild conditions (pH 6.6, 37 degrees C) by enzymatic hydrolysis using papain or lipase M from Mucor javanicus to give building blocks useful for chain-extending glycopeptide synthesis. On the other hand, the selective removal of acetyl protecting groups from the saccharide portion of glycopeptides is accomplished by alternative enzymatic hydrolysis with lipase WG from wheat germ to furnish model substrates for enzymatic glycosyl transfer reactions in order to extend the carbohydrate side chain of these conjugates.
Modeling transpiration and leaf temperature of urban trees – A case study evaluating the microclimate model ENVI-met against measurement data
Abstract Increasing vegetation cover in cities is a key approach to mitigating urban heat excess. However, both the effect of vegetation on microclimate and the plants’ vitality need to be assessed to support and quantify the effects of such strategies. One way to assess the interactions between vegetation and the urban environment is through microclimate models that can simulate the effects of vegetation onto the urban microclimate as well as effects of urban environments onto vegetation. To provide reliable estimates microclimate models need to be parameterized based on empirically obtained data. In this paper we compare modeled transpiration rates and leaf temperatures of a leading micro…
Selektive enzymatische Schutzgruppenabspaltungen: Der n-Heptylester als Carboxylschutzgruppe in der Peptidsynthese
Selective Enzymatic Removal of Protecting Groups: n-Heptyl Esters as Carboxy Protecting Functions in Peptide Synthesis Amino acid heptyl (Hep) esters are accessible as generally crystalline hydro tosylates 3 from the amino acids by azeotropic esterification with 1-heptanol in high yields. They can be condensed with Z-, Boc-, and Aloc-protected amino acids to give the dipeptides 7–9 in the presence of 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ). From the fully protected dipeptides the N-terminal protecting groups are cleaved by chemical methods without affecting the Hep esters. On the other hand, the heptyl esters can be hydrolyzed under mild conditions (pH = 7.0, 37°C) and with hi…
Enzymatische hydrolyse hydrophiler ester durch lipasen - eine milde carboxydeblockierung von peptiden und glycopeptiden
Abstract The markedly hydrophilic 2-(N-morpholino)ethyl (MoEt) esters of protected peptides and glycopeptides are selectively and efficiently cleaved by lipases in water/acetone (10:1) at pH 7.
ChemInform Abstract: Chemoselective Removal of Protecting Groups from O-Glycosyl Amino Acid and Peptide (Methoxyethoxy)ethyl Esters Using Lipases and Papain.
The selective C-terminal deprotection of O-glycopeptide (methoxyethoxy)ethyl esters is achieved under mild conditions (pH 6.6, 37 degrees C) by enzymatic hydrolysis using papain or lipase M from Mucor javanicus to give building blocks useful for chain-extending glycopeptide synthesis. On the other hand, the selective removal of acetyl protecting groups from the saccharide portion of glycopeptides is accomplished by alternative enzymatic hydrolysis with lipase WG from wheat germ to furnish model substrates for enzymatic glycosyl transfer reactions in order to extend the carbohydrate side chain of these conjugates.
Chemoenzymatic synthesis of O-glycopeptides carrying the tumor associated TN-antigen structure
Abstract The application of the lipase-catalyzed C-terminal deprotection of heptyl esters for the construction of acid- and base-labile O -glycopeptides carrying the characteristic structural element of the tumor associated T N -antigen (GalNAc α→Ser/Thr) is described