Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety.

  title={Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety.},
  author={Fernando Filira and Laura Biondi and Franco Cavaggion and Barbara Scolaro and Raniero Rocchi},
  journal={International journal of peptide and protein research},
  volume={36 1},
Synthesis is described of four tuftsin derivatives containing a D-glucopyranosyl or a D-galactopyranosyl unit covalently linked to the hydroxy side chain function of the threonine residue through either an alpha or beta O-glycosidic linkage. Fmoc-threonine derivatives containing the suitable unprotected sugar were used for incorporating the O-glycosylated amino acid residue. Z-Thr[alpha-Glc(OBzl)4]-OBzl and Z-Thr[alpha-Gal(OBzl)4]-OBzl were prepared from the tetra-O-benzylated sugar and Z-Thr… Expand
Synthesis and biological activity of [L‐hydroxyproline]3‐tuftsin analogue and its α‐ or β‐O‐D‐glucosylated derivatives
Syntheses are described of the Hyp3-tuftsin analogue and of its derivatives alpha- or beta-O-glycosylated at the side chain function of the hydroxyproline residue. The carbohydrate-free tetrapeptideExpand
Susceptibility of glycans to beta-elimination in Fmoc-based O-glycopeptide synthesis.
In order to investigate the possible extent of beta-elimination occurring in Fmoc-based continuous-flow solid-phase glycopeptide synthesis, the influence of the pKb of the base used for NExpand
Solid-phase synthesis of glycopeptides: Glycosylation of resin-bound serine-peptides by 3,4,6-tri-o-acetyl-D-glucose-oxazoline
Abstract 3,4,6-Tri-O-acetyl-D-glucose-oxazoline, prepared from 2-acetamido-2-deoxy-1,3,4, 6-tetra-O-acetyl-β-D-glucopyranose with trimethylsilyl trifluoromethanesulfonate, was used forExpand
Synthesis and conformational analysis of N-glycopeptides that contain extended sugar chains
Abstract Maltooligosaccharides with 2–7 sugar moieties were converted into β-1-amino-1-deoxy derivatives and were coupled to Nα-fluorenylmethoxycarbonyl-L-aspartic acid α-tert-butylExpand
Synthesis and biological activity of the mono- and di-galactosyl-vespulakinin 1 analogues.
Preliminary pharmacological experiments showed that the carbohydrate-free vespulakinin 1 is less active than bradykinin when tested by guinea pig rectum contraction, and the two monoglycosylated analogues are equiactive (about 0.9 times the bradykinsin activity). Expand
Chemical and enzymatic synthesis of multivalent sialoglycopeptides.
Linear and branched glycopeptides containing multiple sialyl-N-acetyllactosamine side chains have been synthesized using a combined chemical and enzymatic approach, revealing that most of the multivalent sialoglycopeptide exhibit increased binding that depends on the spacing when compared to monovalent compounds. Expand
Direct synthesis of glycosylated amino acids from carbohydrate peracetates and Fmoc amino acids: solid-phase synthesis of biomedicinally interesting glycopeptides.
This chapter describes solid-phase synthesis of biomedicinally interesting glycopeptides, including the use of peracetylated carbohydrates in Lewis acid-catalyzed glycosylations of 3-mercaptopropionic acid and different Fmoc amino acids. Expand
Synthesis and biological activity of some linear and cyclic kinin analogues.
Preliminary pharmacological experiments showed that the cyclic kinin analogues are much less potent then bradykinin but still show specific brady Kinin-like actions that support the hypothesis of the presence of a pharmacophore in the centre of the (brady)kinin molecule. Expand
The active ester N-fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac3-α-D-Manp-1-]=thre-O-Pfp as a building block in solid-phase synthesis of an o-linked dimannosyl glycopeptide.
Abstract The active ester N α -Fmoc-3-O-[Ac 4 -α-D-Manp-(1-→2)-Ac 3 -α-D-Manp-1-]-Thr-O-Pfp ( 6 ) was synthesized by direct condensation of Ac 4 -α-D-Manp-(1→2)-Ac 3 -α-D-Manp-Br ( 4 ) withExpand
Solid-phase synthesis and characterization of O-dimannosylated heptadecapeptide analogues of human insulin-like growth factor 1 (IGF-1)
N α -Fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac3-α-D-Manp-1-]-Thr-OPfp, 7, and Nα-Fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac3-α-D-Manp-1-]-Ser-OPfp, 8, were prepared and used as building blocks in automatedExpand


Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives.
Glycosylation of the carboxyl function of the C-terminal arginine has been achieved by reacting, through the mixed anhydride procedure, Boc-Thr-Lys(Z)-Pro-OH with 2-deoxy-2-(NG-nitroargininamido)-D-glucopyranose followed by catalytic hydrogenation and trifluoroacetic acid treatment. Expand
The Application of the Trichloroacetimidate Method to the Synthesis of α-D-Gluco- and α-D-Galactopyranosides
Abstract The trichloroacetimidate method has been applied to the construction of α-d-galacto- and α-d-glucopyranosides. The readily available β-trichloroacetimidates ofExpand
Un nouvel agent de glycosylation: l'anhydride trifluorométhanesulfonique. Synthèse des α et β O-glycosyl-L-sérine, -L-thréonine et -L-hydroxyproline
When 2,3,4,6-tetra-O-benzyl-D-glucopyranose, -D-galactopyranose and 2,3,4-tri-O-benzyl-D-xylopyranose were allowed to react in the cold in dichloromethane or acetonitrile as solvent in the presenceExpand
Glycosidation, X. Synthesis of glycoconjugates of acetal-glycosides with lysine and tripeptides for selective cancer therapy
Acetal-glycosides 6 of cytotoxic aldehydes are a new class of compounds which may be of interest for cancer therapy, because of the possibility of a selective release of the cytotoxic principle inExpand
Synthesis of 2-acetamido-1-N[N-(tert-butoxycarbonyl)-l-aspart-1-oyl-(l-phenylalanyl-l-serine methyl ester)-4-oyl]-2-deoxy-β-d-glucopyranosylamine and analogs
Abstract 2-Acetamido-1- N -[ N -( tert -butoxycarbonyl)- l -aspart-1-oyl-( l -phenylalanyl- l -serine methyl ester)-4-oyl]-2-deoxy-β- d -glucopyranosylamine and analogs containing d -glucopyranosyl,Expand
New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]
Glycoproteins, glycolipids, and glycophospholipids (glycoconjugates) are components of membranes. The oligosaccharide residue is responsible for intercellular recognition and interaction; it acts asExpand
Synthesis and biological activity of [Leu5]enkephalin derivatives containing D-glucose.
The obtained results suggest that the opioid activity of the tested glucoconjugates depend upon the ester bond position in the molecule. Expand
Solid-phase peptide synthesis of somatostatin using mild base cleavage of N alpha-9-fluorenylmethyloxycarbonylamino acids.
From several syntheses, analytically pure di-S-protected somatostatin 14-peptide was obtained in 55-60% overall yield and the S-protecting groups were removed and the product was purified by gel filtration to give homogeneous dihydrosom atostatin (91%) yield. Expand
Further Studies on the Use of Multi-substituted Benzenesulfonyl Groups for Protection of the Guanidino Function of Arginine
Various multi-substituted benzenesulfonyl protecting groups for the guanidino function of arginine, removable under mild conditions such as with trifluoroacetic acid (TFA)-thioanisole, were studied.Expand
Solid-phase peptide synthesis using mild base cleavage of N alpha-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin.
N alpha-9-Fluorenylmethyloxycarbonyl (Fmoc) amino acids will be of advantage in solid phase peptide synthesis. The Fmoc-group is quantitatively cleaved by mild base (piperidine). This permits the useExpand