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J Biomol Tech. 2001 September; 12(3): 44–68.
PMCID: PMC2291655

Difficulties encountered during glycopeptide syntheses

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Selected References

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  • Wold F. In vivo chemical modification of proteins (post-translational modification). Annu Rev Biochem. 1981;50:783–814. [PubMed]
  • Helenius A, Aebi M. Intracellular functions of N-linked glycans. Science. 2001 Mar 23;291(5512):2364–2369. [PubMed]
  • Dahms NM, Lobel P, Kornfeld S. Mannose 6-phosphate receptors and lysosomal enzyme targeting. J Biol Chem. 1989 Jul 25;264(21):12115–12118. [PubMed]
  • O'Conner SE, Imperiali B. A molecular basis for glycosylation-induced conformational switching. Chem Biol. 1998 Aug;5(8):427–437. [PubMed]
  • Wyss DF, Wagner G. The structural role of sugars in glycoproteins. Curr Opin Biotechnol. 1996 Aug;7(4):409–416. [PubMed]
  • Wells L, Vosseller K, Hart GW. Glycosylation of nucleocytoplasmic proteins: signal transduction and O-GlcNAc. Science. 2001 Mar 23;291(5512):2376–2378. [PubMed]
  • Gao Y, Wells L, Comer FI, Parker GJ, Hart GW. Dynamic O-glycosylation of nuclear and cytosolic proteins: cloning and characterization of a neutral, cytosolic beta-N-acetylglucosaminidase from human brain. J Biol Chem. 2001 Mar 30;276(13):9838–9845. [PubMed]
  • Hirschberg CB, Snider MD. Topography of glycosylation in the rough endoplasmic reticulum and Golgi apparatus. Annu Rev Biochem. 1987;56:63–87. [PubMed]
  • Kornfeld R, Kornfeld S. Assembly of asparagine-linked oligosaccharides. Annu Rev Biochem. 1985;54:631–664. [PubMed]
  • Sears P, Wong CH. Toward automated synthesis of oligosaccharides and glycoproteins. Science. 2001 Mar 23;291(5512):2344–2350. [PubMed]
  • Pennington MW, Byrnes ME. Procedures to improve difficult couplings. Methods Mol Biol. 1994;35:1–16. [PubMed]
  • O'Connor SE, Pohlmann J, Imperiali B, Saskiawan I, Yamamoto K. Probing the effect of the outer saccharide residues of N-linked glycans on peptide conformation. J Am Chem Soc. 2001 Jun 27;123(25):6187–6188. [PubMed]
  • Kihlberg J, Elofsson M, Salvador LA. Direct synthesis of glycosylated amino acids from carbohydrate peracetates and Fmoc amino acids: solid-phase synthesis of biomedicinally interesting glycopeptides. Methods Enzymol. 1997;289:221–245. [PubMed]
  • Bertozzi CR, Kiessling LL. Chemical glycobiology. Science. 2001 Mar 23;291(5512):2357–2364. [PubMed]
  • Otvos L, Jr, Wroblewski K, Kollat E, Perczel A, Hollosi M, Fasman GD, Ertl HC, Thurin J. Coupling strategies in solid-phase synthesis of glycopeptides. Pept Res. 1989 Nov-Dec;2(6):362–366. [PubMed]
  • Filira F, Biondi L, Cavaggion F, Scolaro B, Rocchi R. Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety. Int J Pept Protein Res. 1990 Jul;36(1):86–96. [PubMed]
  • Sjölin Petter, Elofsson Mikael, Kihlberg Jan. Removal of Acyl Protective Groups from Glycopeptides: Base Does Not Epimerize Peptide Stereocenters, and beta-Elimination Is Slow. J Org Chem. 1996 Jan 26;61(2):560–565. [PubMed]
  • Oegema TR, Jr, Kraft EL, Jourdian GW, Van Valen TR. Phosphorylation of chondroitin sulfate in proteoglycans from the swarm rat chondrosarcoma. J Biol Chem. 1984 Feb 10;259(3):1720–1726. [PubMed]
  • Moses J, Oldberg A, Cheng F, Fransson LA. Biosynthesis of the proteoglycan decorin--transient 2-phosphorylation of xylose during formation of the trisaccharide linkage region. Eur J Biochem. 1997 Sep 1;248(2):521–526. [PubMed]
  • Bourdon MA, Krusius T, Campbell S, Schwartz NB, Ruoslahti E. Identification and synthesis of a recognition signal for the attachment of glycosaminoglycans to proteins. Proc Natl Acad Sci U S A. 1987 May;84(10):3194–3198. [PubMed]
  • Andrews DM, Seale PW. Solid-phase synthesis of O-mannosylated peptides: two strategies compared. Int J Pept Protein Res. 1993 Aug;42(2):165–170. [PubMed]
  • Rio S, Beau JM, Jacquinet JC. Synthesis of sulfated and phosphorylated glycopeptides from the carbohydrate-protein linkage region of proteoglycans. Carbohydr Res. 1994 Mar 4;255:103–124. [PubMed]
  • Rio S, Beau JM, Jacquinet JC. Total synthesis of the carbohydrate-protein linkage region common to several mammalian proteoglycans. Carbohydr Res. 1993 Jun 21;244(2):295–313. [PubMed]
  • Meldal M, Bielfeldt T, Peters S, Jensen KJ, Paulsen H, Bock K. Susceptibility of glycans to beta-elimination in Fmoc-based O-glycopeptide synthesis. Int J Pept Protein Res. 1994 Jun;43(6):529–536. [PubMed]
  • Butler WT, Cunningham LW. Evidence for the linkage of a disaccharide to hydroxylysine in tropocollagen. J Biol Chem. 1966 Sep 10;241(17):3882–3888. [PubMed]
  • Spiro RG. Characterization and quantitative determination of the hydroxylysine-linked carbohydrate units of several collagens. J Biol Chem. 1969 Feb 25;244(4):602–612. [PubMed]
  • Chelberg MK, McCarthy JB, Skubitz AP, Furcht LT, Tsilibary EC. Characterization of a synthetic peptide from type IV collagen that promotes melanoma cell adhesion, spreading, and motility. J Cell Biol. 1990 Jul;111(1):261–270. [PMC free article] [PubMed]
  • Fields CG, Mickelson DJ, Drake SL, McCarthy JB, Fields GB. Melanoma cell adhesion and spreading activities of a synthetic 124-residue triple-helical "mini-collagen". J Biol Chem. 1993 Jul 5;268(19):14153–14160. [PubMed]
  • Fields GB, Lauer JL, Dori Y, Forns P, Yu YC, Tirrell M. Protein-like molecular architecture: biomaterial applications for inducing cellular receptor binding and signal transduction. Biopolymers. 1998;47(2):143–151. [PubMed]
  • Miles AJ, Skubitz AP, Furcht LT, Fields GB. Promotion of cell adhesion by single-stranded and triple-helical peptide models of basement membrane collagen alpha 1(IV)531-543. Evidence for conformationally dependent and conformationally independent type IV collagen cell adhesion sites. J Biol Chem. 1994 Dec 9;269(49):30939–30945. [PubMed]
  • Miles AJ, Knutson JR, Skubitz AP, Furcht LT, McCarthy JB, Fields GB. A peptide model of basement membrane collagen alpha 1 (IV) 531-543 binds the alpha 3 beta 1 integrin. J Biol Chem. 1995 Dec 8;270(49):29047–29050. [PubMed]
  • Li C, McCarthy JB, Furcht LT, Fields GB. An all-D amino acid peptide model of alpha1(IV)531-543 from type IV collagen binds the alpha3beta1 integrin and mediates tumor cell adhesion, spreading, and motility. Biochemistry. 1997 Dec 9;36(49):15404–15410. [PubMed]
  • Lauer JL, Gendron CM, Fields GB. Effect of ligand conformation on melanoma cell alpha3beta1 integrin-mediated signal transduction events: implications for a collagen structural modulation mechanism of tumor cell invasion. Biochemistry. 1998 Apr 14;37(15):5279–5287. [PubMed]
  • Vogel W, Gish GD, Alves F, Pawson T. The discoidin domain receptor tyrosine kinases are activated by collagen. Mol Cell. 1997 Dec;1(1):13–23. [PubMed]
  • ZAHN H, UMLAUF E. Uber Oxylysin. Hoppe Seylers Z Physiol Chem. 1954;297(3-6):127–145. [PubMed]
  • Broddefalk Johan, Forsgren Mattias, Sethson Ingmar, Kihlberg Jan. Preparation of a Diglycosylated Hydroxylysine Building Block Used in Solid-Phase Synthesis of a Glycopeptide from Type II Collagen. J Org Chem. 1999 Nov 26;64(24):8948–8953. [PubMed]
  • Nukada T, Kitajima T, Nakahara Y, Ogawa T. Synthesis of an octasaccharide fragment of high-mannose-type glycans of glycoproteins. Carbohydr Res. 1992 Apr 10;228(1):157–170. [PubMed]
  • Babel W, Glanville RW. Structure of human-basement-membrane (type IV) collagen. Complete amino-acid sequence of a 914-residue-long pepsin fragment from the alpha 1(IV) chain. Eur J Biochem. 1984 Sep 17;143(3):545–556. [PubMed]
  • Bodanszky M, Kwei JZ. Side reactions in peptide synthesis. VII. Sequence dependence in the formation of aminosuccinyl derivatives from beta-benzyl-aspartyl peptides. Int J Pept Protein Res. 1978 Aug;12(2):69–74. [PubMed]
  • Tam JP, Riemen MW, Merrifield RB. Mechanisms of aspartimide formation: the effects of protecting groups, acid, base, temperature and time. Pept Res. 1988 Sep-Oct;1(1):6–18. [PubMed]
  • Wang ZG, Zhang X, Live D, Danishefsky SJ. From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide This work was supported by the National Institutes of Health (Grant Numbers AI16943/CA28824). We thank Dr. George Sukenick of the MSKCC NMR Core Facility for NMR and mass spectral analyses (NIH Grant Number: CA08748). Angew Chem Int Ed Engl. 2000 Oct 16;39(20):3652–3656. [PubMed]
  • Bodanszky M, Tolle JC, Deshmane SS, Bodanszky A. Side reactions in peptide synthesis. VI. A reexamination of the benzyl group in the protection of the side chains of tyrosine and aspartic acid. Int J Pept Protein Res. 1978 Aug;12(2):57–68. [PubMed]
  • Wittelsberger A, Keller M, Scarpellino L, Patiny L, Acha-Orbea H, Mutter M. Pseudoprolines: Targeting a cis Conformation in a Mimetic of the gp120 V3 Loop of HIV-1 We are grateful to Dipl.-Biol. Raymond Jacquet for helpful advice. This work was supported by the Swiss National Science Foundation. Angew Chem Int Ed Engl. 2000 Mar;39(6):1111–1115. [PubMed]

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