Synthesis of mucin-type glycopeptide (β hCG 130–145) by on-resin fragment condensation of the glycopeptide segments carrying unmasked oligosaccharides

Ichiyanagi, Tsuyoshi; Takatani, Maki; Sakamoto, Kimitoshi; Nakahara, Yuko; Ito, Yukishige; Hojo, Hironobu; Nakahara, Yoshiaki

doi:10.1016/s0040-4039(02)00542-7

Cited by 21 publications

(8 citation statements)

References 37 publications

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“…in 1993, which described a solid phase glycopeptide synthesis from glycoamino acid containing unprotected O-glycans 37. This approach has since been employed in the synthesis of a few simple glycopeptides with some success 38-40. On the basis of this work, we considered the possibility of utilizing a similar strategy to prepare our O-glycopeptide.…”

Section: Resultsmentioning

confidence: 99%

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain

et al. 2009

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Single erythropoietin (EPO) glycoforms with defined mature oligosaccharide structures and amino acid sequences are essential to elucidate the molecular mechanisms by which carbohydrates exert various physiological and metabolic functions and to explore the possible links between carbohydrates and the prevention or management of diseases. To demonstrate that it is possible to generate EPO even without recourse to cysteine-based NCL, a concise synthesis of the partially-protected EPO fragment (78-166) bearing fully mature N- and O-glycans is described.

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Section: Resultsmentioning

confidence: 99%

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain

et al. 2009

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“…In order to avoid problems with deprotection of glycans in newly synthesized glycoproteins, Ichiyanagi et al (2002) have deprotected b-Gal-(1 ! 3)-GalNAc attached to serine and used this molecule in glycopeptide synthesis using FMOC coupling.…”

Section: B Synthesis Of Carbohydrate-protein Complexesmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Harvey¹

2008

Mass Spectrometry Reviews

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This review is the second update of the original review on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates that was published in 1999. It covers fundamental aspects of the technique as applied to carbohydrates, fragmentation of carbohydrates, studies of specific carbohydrate types such as those from plant cell walls and those attached to proteins and lipids, studies of glycosyl-transferases and glycosidases, and studies where MALDI has been used to monitor products of chemical synthesis. Use of the technique shows a steady annual increase at the expense of older techniques such as FAB. There is an increasing emphasis on its use for examination of biological systems rather than on studies of fundamental aspects and method development and this is reflected by much of the work on applications appearing in tabular form.

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“…Human chorionic gonadotropin (hCG) was selected as a target. We successfully synthesized a fragment of βhCG having 2 sugar chains (60). For the elongation of a glycopeptide with an unprotected sugar chain, In solid phase peptide synthesis, the formation of diketopiperadine is often a problem.…”

Section: C-5 Studies Of the Synthesis Of Glycoproteinsmentioning

confidence: 99%

My Stroll in the Backyard of Carbohydrate Chemistry

Ito

2010

TIGG

Self Cite

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The fields of "Glycobiology" and "Glycotechnology" are gaining an increasing amount of attention. A major part of my research has been directed at the synthesis and functional analysis of glycoconjugate oligosaccharides of various origins. In this mini-review, I wish to summarize my research history in carbohydrate chemistry of the last 12 years. Representative subjects have been 1) synthetic studies on Asn-linked glycan chains, 2) synthesis of novel glycoprotein structures, 3) approaches to polymer-support synthesis of oligosaccharides, 4) development of new reactions for the synthesis of glycoprotein-related molecules, 5) studies on the synthesis of glycoproteins, 6) analyses of glycoprotein processing and protein quality control system, 7) synthesis of glycosyltransferase inhibitors, 8) synthesis of biologically active glycolipids, and 9) synthesis and biological activities on mycobacterial cell wall components.

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Synthesis of mucin-type glycopeptide (β hCG 130–145) by on-resin fragment condensation of the glycopeptide segments carrying unmasked oligosaccharides

Cited by 21 publications

References 37 publications

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

My Stroll in the Backyard of Carbohydrate Chemistry

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Synthesis of mucin-type glycopeptide (β hCG 130–145) by on-resin fragment condensation of the glycopeptide segments carrying unmasked oligosaccharides

Cited by 21 publications

References 37 publications

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln78−Arg166 Glycopeptide Domain

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln78−Arg166 Glycopeptide Domain

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

My Stroll in the Backyard of Carbohydrate Chemistry

Contact Info

Product

Resources

About

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain

Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln⁷⁸−Arg¹⁶⁶ Glycopeptide Domain