クリックケミストリーを利用した炭水化物誘導体

Iris Biotech社の試薬、クリックケミストリーを利用した炭水化物誘導体をご紹介しております。



タンパク質および脂質への糖鎖付加は生命を支配する普遍的なプロセスです。糖の付加はタンパク質の折り畳みおよび安定化に影響を及ぼすとともに糖化合物はエネルギー貯蔵、細胞間コミュニケーションのための分子識別モチーフを介する細胞表面相互作用、そして細胞の構造的サポートや保護等の多数の生物学的効果を示します。

疾病の発症プロセス、炎症および微生物感染によって問題が生じた代謝経路、神経変性または腫瘍転移などのキーワードで代表される分野だけではなく、多くの分野に関わりがあります。クリック反応の確実性と特異性により、薬剤およびワクチン開発の使用において、これまで困難であった炭水化物との結合を含む分子のデザインが可能になります。

参考文献

▷ Essentials of Glycobiology; A. Varki, R. Cummins, J. Esko, H. Freeze, G. Hart and J. Marth; Cold Spring Harbor Laboratory Press; Cold Spring Harbor 1999.

▷ Role of glycosylation in development; R. S. Haltiwanger and J. B. Lowe; Annu Rev Biochem 2004; 73, 491-537.

▷ Glycosylation and the immune system; P. M. Rudd, T. Elliott, P. Cresswell, I. A. Wilson and R. A. Dwek; Science 2001; 291, 2370-6.

▷ Glycosylation in cellular mechanisms of health and disease; K. Ohtsubo and J. D. Marth; Cell 2006; 126, 855-67.

▷ The role of selectins in inflammation and disease; K. Ley; Trends Mol Med 2003; 9, 263-8.

▷ Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates; A. Holemann and P. H. Seeberger; Curr Opin Bio-technol 2004; 15, 615-22.

▷ Post-translational modifications in the context of therapeutic prote-ins; G. Walsh and R. Jefferis; Nat Biotechnol 2006; 24, 1241-52.

▷ Glycomics: a pathway to a class of new and improved therapeutics; Z. Shriver, S. Raguram and R. Sasisekharan; Nat Rev Drug Discov 2004; 3, 863-73.

▷ The bittersweet promise of glycobiology; A. Dove; Nat Biotechnol2001; 19, 913-7.

▷ Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions; X. L. Sun, C. L. Stabler, C. S. Cazalis and E. L. Chaikof; Bioconjug Chem 2006; 17, 52-7.

▷ Covalent display of oligosaccharide arrays in microtiter plates; M. C. Bryan, F. Fazio, H. K. Lee, C. Y. Huang, A. Chang, M. D. Best, D. A. Calarese, O. Blixt, J. C. Paulson, D. Burton, I. A. Wilson and C. H. Wong; J Am Chem Soc 2004; 126, 8640-1.

▷ Multivalent, bifunctional dendrimers prepared by click chemistry; P. Wu, M. Malkoch, J. N. Hunt, R. Vestberg, E. Kaltgrad, M. G. Finn, V. V. Fokin, K. B. Sharpless and C. J. Hawker; Chem Commun (Camb) 2005, 5775-7.

▷ A chemoenzymatic approach to glycopeptide antibiotics; H. Lin and C. T. Walsh; J Am Chem Soc 2004; 126, 13998-4003.

製品一覧

ガラクトース誘導体


表1. ガラクトース誘導体製品一覧
コード 製品名 分子式 CAS 分子量 内容量 名称
GBB1207.0001 D-Gal(N3, Ac3)-OAc C14H19N3O9 84278-00-2 373.32 1g 2-Azido-2-deoxy-1,3,4,6-tetra-O-acetyl-alpha/beta-D-galactopyranose
GBB1207.0002 D-Gal(N3, Ac3)-OAc C14H19N3O9 84278-00-2 373.32 2g 2-Azido-2-deoxy-1,3,4,6-tetra-O-acetyl-alpha/beta-D-galactopyranose
GBB1207.0250 D-Gal(N3, Ac3)-OAc C14H19N3O9 84278-00-2 373.32 250mg 2-Azido-2-deoxy-1,3,4,6-tetra-O-acetyl-alpha/beta-D-galactopyranose
GBB1370.0000 alpha-GalNAc-TEG-N3 C14H26N4O8 - 378.38 0 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1375.0100 alpha-GalNAc-TEG-Alkyne C17H29NO9 - 391.41 100mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1375.0250 alpha-GalNAc-TEG-Alkyne C17H29NO9 - 391.41 250mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1375.0500 alpha-GalNAc-TEG-Alkyne C17H29NO9 - 391.41 500mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1375.1000 alpha-GalNAc-TEG-Alkyne C17H29NO9 - 391.41 1g 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1380.0100 beta-Gal-TEG-N3 C12H23N3O8 - 337.33 100mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-beta-D-galactopyranoside
GBB1380.0250 beta-Gal-TEG-N3 C12H23N3O8 - 337.33 250mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-beta-D-galactopyranoside
GBB1385.0000 beta-Gal-TEG-Alkyne C15H26O9 - 350.36 0 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-beta-D-galactopyranoside
GBB1430.0100 beta-Gal-N3 C8H15N3O6 - 249.22 100mg 1-(2-Azidoethoxy)-beta-D-galactopyranose
GBB1430.0250 beta-Gal-N3 C8H15N3O6 - 249.22 250mg 1-(2-Azidoethoxy)-beta-D-galactopyranose
GBB1430.0500 beta-Gal-N3 C8H15N3O6 - 249.22 500mg 1-(2-Azidoethoxy)-beta-D-galactopyranose
GBB1430.1000 beta-Gal-N3 C8H15N3O6 - 249.22 1g 1-(2-Azidoethoxy)-beta-D-galactopyranose
GBB1445.0050 alpha-GalNAc-N3 C10H18N4O6 - 290.27 50mg 1-O-(2-Azidoethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1445.0100 alpha-GalNAc-N3 C10H18N4O6 - 290.27 100mg 1-O-(2-Azidoethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1445.0250 alpha-GalNAc-N3 C10H18N4O6 - 290.27 250mg 1-O-(2-Azidoethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1445.0500 alpha-GalNAc-N3 C10H18N4O6 - 290.27 500mg 1-O-(2-Azidoethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside
GBB1460.0001 Azido-beta-Gal(Ac4) C14H19N3O9 13992-26-2 373.32 1g 2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl azide
GBB1460.0002 Azido-beta-Gal(Ac4) C14H19N3O9 13992-26-2 373.32 2g 2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl azide
GBB1460.0005 Azido-beta-Gal(Ac4) C14H19N3O9 13992-26-2 373.32 5g 2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl azide
GBB1470.0001 Azido-alpha-Gal(Ac4) C14H19N3O9 94427-00-6 373.32 1g 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl azide
GBB1470.0002 Azido-alpha-Gal(Ac4) C14H19N3O9 94427-00-6 373.32 2g 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl azide

グルコース誘導体


表2. グルコース誘導体製品一覧
コード 製品名 分子式 CAS 分子量 内容量 名称
GBB1390.0000 beta-Glc-TEG-N3 C12H23N3O8 - 337.33 0 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-beta-D-glucopyranoside
GBB1395.0000 beta-Glc-TEG-Alkyne C15H26O9 - 350.36 0 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-beta-D-glucopyranoside
GBB1400.0100 beta-GlcNAc-TEG-N3 C14H26N4O8 - 378.73 100mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1400.0250 beta-GlcNAc-TEG-N3 C14H26N4O8 - 378.73 250mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1400.0500 beta-GlcNAc-TEG-N3 C14H26N4O8 - 378.73 500mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1405.0250 beta-GlcNAc-TEG-Alkyne C17H29NO9 - 391.41 250mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1405.0500 beta-GlcNAc-TEG-Alkyne C17H29NO9 - 391.41 500mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1405.1000 beta-GlcNAc-TEG-Alkyne C17H29NO9 - 391.41 1g 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-2-acetamido-2deoxy-beta-D-glucopyranoside
GBB1435.0000 beta-Glc-N3 C8H15N3O6 - 249.22 0 1-(2-Azidoethoxy)-beta-D-glucopyranose
GBB1450.0000 beta-GlcNAc-N3 C10H18N4O6 - 290.27 0 1-(2-Azidoethoxy)-2-acetamido-2deoxy-beta-D-galactopyranose
GBB1465.0001 Azido-beta-Glc(Ac4) C14H19N3O9 13992-25-1 373.32 1g 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide
GBB1465.0002 Azido-beta-Glc(Ac4) C14H19N3O9 13992-25-1 373.32 2g 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide
GBB1465.0005 Azido-beta-Glc(Ac4) C14H19N3O9 13992-25-1 373.32 5g 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide
GBB1475.0001 D-Glc(Ac4)-beta-PEG(3)-N3 C20H31N3O12 - 505.47 1g 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl PEG(3)-azide
GBB1475.0002 D-Glc(Ac4)-beta-PEG(3)-N3 C20H31N3O12 - 505.47 2g 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl PEG(3)-azide

マンノース誘導体


表3. マンノース誘導体製品一覧
コード 製品名 分子式 CAS 分子量 内容量 名称
GBB1222.0050 beta-D-Man(N3, Ac3)-OMe C13H19N3O8 - 345.34 50mg Methyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-mannopyranoside
GBB1222.0100 beta-D-Man(N3, Ac3)-OMe C13H19N3O8 - 345.34 100mg Methyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-mannopyranoside
GBB1222.0250 beta-D-Man(N3, Ac3)-OMe C13H19N3O8 - 345.34 250mg Methyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-mannopyranoside
GBB1410.0000 beta-Lac-TEG-N3 C18H33N3O13 - 499.47 0 -
GBB1415.0000 beta-Lac-TEG-Alkyne C21H36O14 - 512.5 0 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-beta-D-lactoside
GBB1420.0100 alpha-Man-TEG-N3 C12H23N3O8 - 337.33 100mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-alpha-D-mannopyranoside
GBB1420.0250 alpha-Man-TEG-N3 C12H23N3O8 - 337.33 250mg 1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-alpha-D-mannopyranoside
GBB1425.0100 alpha-Man-TEG-Alkyne C15H26O9 - 350.36 100mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-alpha-D-mannopyranoside
GBB1425.0250 alpha-Man-TEG-Alkyne C15H26O9 - 350.36 250mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-alpha-D-mannopyranoside
GBB1425.0500 alpha-Man-TEG-Alkyne C15H26O9 - 350.36 500mg 1-O-(2-(2-(2-(Prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)-alpha-D-mannopyranoside
GBB1440.0100 alpha-Man-N3 C8H15N3O6 - 249.22 100mg 1-(2-Azidoethoxy)-alpha-D-mannopyranose
GBB1440.0250 alpha-Man-N3 C8H15N3O6 - 249.22 250mg 1-(2-Azidoethoxy)-alpha-D-mannopyranose
GBB1440.0500 alpha-Man-N3 C8H15N3O6 - 249.22 500mg 1-(2-Azidoethoxy)-alpha-D-mannopyranose
GBB1440.1000 alpha-Man-N3 C8H15N3O6 - 249.22 1g 1-(2-Azidoethoxy)-alpha-D-mannopyranose
GBB1455.0100 beta-Lac-EO-N3 C14H25N3O11 - 411.36 100mg 1-(2-Azidoethoxy)-beta-D-lactose
GBB1455.0250 beta-Lac-EO-N3 C14H25N3O11 - 411.36 250mg 1-(2-Azidoethoxy)-beta-D-lactose
GBB1455.0500 beta-Lac-EO-N3 C14H25N3O11 - 411.36 500mg 1-(2-Azidoethoxy)-beta-D-lactose
GBB1455.1000 beta-Lac-EO-N3 C14H25N3O11 - 411.36 1g 1-(2-Azidoethoxy)-beta-D-lactose
GBB1480.0100 D-Lac-beta-N3 C12H21N3O10 69266-16-6 367.31 100mg 1-Azido-1-deoxy-beta-D-lactopyranoside
GBB1480.0250 D-Lac-beta-N3 C12H21N3O10 69266-16-6 367.31 250mg 1-Azido-1-deoxy-beta-D-lactopyranoside
GBB1480.0500 D-Lac-beta-N3 C12H21N3O10 69266-16-6 367.31 500mg 1-Azido-1-deoxy-beta-D-lactopyranoside
GBB1490.0001 Mal(Ac7)-beta-N3 C26H35N3O17 33012-49-6 661.57 1g 2,3,4,6,2',3',6'-Hepta-O-acetyl-beta-maltosyl azide
GBB1490.0002 Mal(Ac7)-beta-N3 C26H35N3O17 33012-49-6 661.57 2g 2,3,4,6,2',3',6'-Hepta-O-acetyl-beta-maltosyl azide
GBB1490.0005 Mal(Ac7)-beta-N3 C26H35N3O17 33012-49-6 661.57 5g 2,3,4,6,2',3',6'-Hepta-O-acetyl-beta-maltosyl azide