Azidonitration of Di-O-acetyl-L-fucal: X-Ray Crystal Structures of Intermediate Azidodeoxysugars and of the Bacterial Aminosugar N-Acetyl-L-fucosamine

被引：6

作者：

Alhassan, Abdul-Basit ^{[1
]}

McCutcheon, David C. ^{[1
]}

Zeller, Matthias ^{[1
]}

Norris, Peter ^{[1
]}

机构：

[1] Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2012年 / 31卷 / 4-6期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

Azidonitration; L-Fucal; N-Acetyl-L-fucosamine; Aminosugar; X-ray structure; BIOSYNTHESIS;

D O I：

10.1080/07328303.2012.658125

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The azidonitration of di-O-acetyl-L-fucal has previously been shown to be an efficient route to the bacterial aminosugar N-acetyl-L-fucosamine. Upon repeating this sequence, with updated versions of the glycal formation and amide installation steps, we have obtained X-ray crystal structures of several of the addition products, which are now reported along with the solid-state structure of N-acetyl-L-fucosamine itself.

引用

页码：371 / 383

页数：13

共 15 条

[1] Synthesis and activity of dipeptides, linked to targeting ligands, as specific NK cell enhancers [J].

Abbott, SD ;

Gagnon, L ;

Lagraoui, M ;

Kadhim, S ;

Attardo, G ;

Zacharie, B ;

Penney, CL .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (11) :1909-1926

[2] PREPARATIVE SYNTHESIS OF 2-ACETAMIDO-2,6-DIDEOXY-L-GALACTOSE (N-ACETYL-L-FUCOSAMINE) [J].

ANISUZZAMAN, AKM ;

HORTON, D .

CARBOHYDRATE RESEARCH, 1987, 169 :258-262

[3]

[Anonymous], 2002, SMART 5 630

[4]

[Anonymous], 2003, SAINT 6 45

[5]

[Anonymous], 2003, SHELXTL VERS 6 14

[6] Bronsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins [J].

Balthaser, Bradley R. ;

McDonald, Frank E. .

ORGANIC LETTERS, 2009, 11 (21) :4850-4853

[7] SYNTHESIS OF 2,6-DIDEOXY-ALPHA-L-LYXO-HEXOPYRANOSYL HALIDES AND 2,6-DIDEOXY-ALPHA-L-ARABINO-HEXOPYRANOSYL HALIDES [J].

ELKHADEM, HS ;

SWARTZ, DL ;

NELSON, JK ;

BERRY, LA .

CARBOHYDRATE RESEARCH, 1977, 58 (01) :230-234

[8] Development of a catalytic cycle for the generation of C1-glycosyl carbanions with Cp2TiCl2:: application to glycal synthesis [J].

Hansen, T ;

Daasbjerg, K ;

Skrydstrup, T .

TETRAHEDRON LETTERS, 2000, 41 (44) :8645-8649

[9] Three highly conserved proteins catalyze the conversion of UDP-N-acetyl-D-glucosamine to precursors for the biosynthesis of O antigen in Pseudomonas aeruginosa 011 and capsule in Staphylococcus aureus type 5 [J].

Kneidinger, B ;

O'Riordan, K ;

Li, JJ ;

Brisson, JR ;

Lee, JC ;

Lam, JS .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (06) :3615-3627

[10] Reaktionen enolischer Zuckerderivate, XIV. Eine neue Synthese von L-Fucosamin durch „Azidonitratisierung︁ von L-Fucal [J].

Lehmann, Jochen ;

Reutter, Werner ;

Schöning, Dietgard .

European Journal of Inorganic Chemistry, 1979, 112 (04) :1470-1472

← 1 2 →