Synthesis of N-Linked Glycosyl Asparagine Derivatives with Unprotected Sugar Components

Akihiro Ishiwata; Maki Takatani; Yoshiaki Nakahara; Yukishige Ito

doi:10.1055/s-2002-22716

LETTER

Synthesis of N-Linked Glycosyl Asparagine Derivatives with Unprotected Sugar Components

Akihiro Ishiwata^a, Maki Takatani^a, Yoshiaki Nakahara^a,b, Yukishige Ito*^a
^a RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
^b Department of Applied Biochemistry, Tokai University, Hiratsuka-shi, Kanagawa 259-1292 Japan
Fax: +81(48)4624680; e-Mail: yukito@postman.riken.go.jp;

Abstract

Alle Artikel dieser Rubrik

Abstract

A general methodology for the efficient formation of N-glycosidic linkage to asparagine (Asn), which, does not require the protection of sugar component hydroxyl groups is described. Aspartic acid fluoride was used in combination with N-allyloxycarbonyl (Alloc) glycosyl amines. Pd(0)-PhSiH₃ mediated in situ Alloc removal-coupling was performed in aqueous solution dioxane to give Asn-linked carbohydrates in high yield.

Key words

asparagine - carbohydrate - aspartic acid fluoride - glycosylamine - allyl carbamate

Volltext

Referenzen

References

<A NAME="RY00502ST-1A">1a</A> Dwek R. Chem. Rev. 1996, 96: 683

<A NAME="RY00502ST-1B">1b</A> Essentials in Glyocbiology Varki A. Cummings R. Esko J. Freeze H. Hart G. Marth J. Cold Spring Harbor Laboratory Press; New York: 1999.

Recent reviews:

<A NAME="RY00502ST-2A">2a</A> Taylor CM. Tetrahedron 1998, 54: 11317

<A NAME="RY00502ST-2B">2b</A> Arsequell G. Valencia G. Tetrahedron: Asymmetry 1999, 10: 3045

<A NAME="RY00502ST-2C">2c</A> Mizuno M. Trends Glycoside Glycotechnol. 2001, 13: 11

<A NAME="RY00502ST-3A">3a</A> Györgydeák Z. Szilágyi L. Paulsen H. J. Carbohydr. Chem. 1993, 12: 139

<A NAME="RY00502ST-3B">3b</A> Matsuo I. Nakahara Y. Ito Y. Nukada T. Nakahara Y. Ogawa T. Bioorg. Med. Chem. 1995, 3: 1455

<A NAME="RY00502ST-3C">3c</A> Inazu T. Kobayashi K. Synlett 1993, 869

<A NAME="RY00502ST-4A">4a</A> Likhosherstov LM. Novikova OS. Derevitskaja VA. Kochetkov NK. Carbohydr. Res. 1986, 146: c1

<A NAME="RY00502ST-4B">4b</A> Lubineau A. Augé J. Droillat B. Carbohydr. Res. 1995, 266: 211

Recent examples:

<A NAME="RY00502ST-5A">5a</A> Campa C. Donati I. Vetere A. Gamini A. Paoletti S. J. Carbohydr. Chem. 2001, 20: 263

<A NAME="RY00502ST-5B">5b</A> Meinjohanns E. Meldal M. Paulsen H. Dwek R. Bock K. J. Chem. Soc., Perkin Trans. 1 1998, 549

<A NAME="RY00502ST-5C">5c</A> Stubbs H. Shia M. Rice K. Anal. Biochem. 1997, 247: 357

<A NAME="RY00502ST-5D">5d</A> Mononen I. Ivanov G. Stoineva IB. Noronkoski T. Petkov DD. Biochem. Biophys. Res. Commun. 1996, 218: 510

<A NAME="RY00502ST-5E">5e</A> Arsequell G. Dwek R. Wong SYC. Anal. Biochem. 1994, 216: 165

<A NAME="RY00502ST-5F">5f</A> Manger ID. Rademacher TW. Dwek RA. Biochemistry 1992, 31: 10724

<A NAME="RY00502ST-5G">5g</A> Wong SYC. Rademacher TW. Dwek RA. Biochemistry 1992, 31: 10733

<A NAME="RY00502ST-5H">5h</A> Cohen-Anisfeld ST. Lamsbury PT. J. Am. Chem. Soc. 1993, 115: 10531

<A NAME="RY00502ST-6">6</A> More recently, purification of glycosylamine by electrodialytic desalting was reported. See: Tokuda Y. Takahashi Y. Matoishi K. Ito Y. Sugai T. Synlett 2002, 57

<A NAME="RY00502ST-7A">7a</A> Carpino LA. Mansour ME. J. Org. Chem. 1992, 57: 6371

<A NAME="RY00502ST-7B">7b</A> Carpino LA. Beyermann M. Wenschuh H. Bienert M. Acc. Chem. Res. 1996, 29: 268

<A NAME="RY00502ST-8">8</A> Ito Y. Gerz M. Nakahara Y. Tetrahedron Lett. 2000, 41: 1039

<A NAME="RY00502ST-9A">9a</A> Thieriet N. Alsina J. Giralt E. Guibé F. Albericio F. Tetrahedron Lett. 1997, 38: 7275

<A NAME="RY00502ST-9B">9b</A> Thieriet N. Pgomez-Martinez P. Guibé F. Tetrahedron Lett. 1999, 40: 2505