An Efficient Synthesis of a Dimer of the Tetrasaccharide Present in Motif B of the Mycobacterium tuberculosis Cell Wall

Xiangdong Mei; Jun Ning

doi:10.1055/s-2005-872674

LETTER

An Efficient Synthesis of a Dimer of the Tetrasaccharide Present in Motif B of the Mycobacterium tuberculosis Cell Wall

Xiangdong Mei^a, Jun Ning*^a,b
^a Research Center for Eco-Environmental Sciences, Academia Sinica, P. O. Box 2871, Beijing 100085, P. R. China
Fax: +86(10)62923563; e-Mail: jning@mail.rcees.ac.cn;
^b Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100094, P. R. China

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient method for the synthesis of 3,5-branched octaarabinoside, which is a dimer of the tetrasaccharide present in motif B of the Mycobacterium tuberculosis cell wall, has been developed by using 2,3,5-tri-O-benzoyl-α-d-arabinofuranosyl trichloroacetimidate, 5-O-acetyl-2,3-di-O-benzoyl-α-d-arabinofuranosyl trichloroacetimidate, 1,2-O-isopropylidene-5-O-trityl-β-d-arabinofuranose, dodecyl 2,3-di-O- benzoyl-α-d-arabinofuranoside and phenyl 2,3-di-O-benzoyl-1-thio-α-d-arabinofuranoside as synthons.

Key words

oligosaccharides - synthesis - glycosylations - stereoselectivity - glycosides

Volltext

Referenzen

References

<A NAME="RU22205ST-1A">1a</A> Sears P. Wong CH. Cell. Mol. Life Sci. 1998, 54: 233

<A NAME="RU22205ST-1B">1b</A> Varki A. Glycobiology 1993, 3: 97

<A NAME="RU22205ST-1C">1c</A> Lis H. Sharon N. Eur. J. Biochem. 1993, 218: 1

<A NAME="RU22205ST-1D">1d</A> Kolter T. Sandhoff K. Angew. Chem. Int. Ed. 1999, 38: 1532

<A NAME="RU22205ST-2">2</A> Sears P. Wong CH. Science 2001, 291: 2433

<A NAME="RU22205ST-3A">3a</A> Ning J. Yi Y. Kong F. Tetrahedron Lett. 2002, 43: 5545

<A NAME="RU22205ST-3B">3b</A> Ning J. Zhang W. Yi Y. Yang G. Wu Z. Yi Z. Kong F. Bioorg. Med. Chem. 2003, 11: 2193

<A NAME="RU22205ST-4A">4a</A> Xing Y. Ning J. Tetrahedron: Asymmetry 2003, 14: 1275

<A NAME="RU22205ST-4B">4b</A> Ning J. Heng L. Kong F. Tetrahedron Lett. 2002, 43: 673

<A NAME="RU22205ST-5">5</A> Ning J. Yi Y. Yao Z. Synlett 2003, 2208

<A NAME="RU22205ST-6A">6a</A> Ning J. Wang H. Yi Y. Tetrahedron Lett. 2002, 43: 7349

<A NAME="RU22205ST-6B">6b</A> Wang H. Ning J. J. Org. Chem. 2003, 68: 2521

<A NAME="RU22205ST-7">7</A> Rademann J. Angew. Chem. Int. Ed. 1998, 37: 1241

<A NAME="RU22205ST-8">8</A> Liang R. Science 1996, 274: 1520

<A NAME="RU22205ST-9A">9a</A> Martin TJ. Tetrahedron Lett. 1992, 33: 6123

<A NAME="RU22205ST-9B">9b</A> Kondo H. J. Am. Chem. Soc. 1992, 114: 8748

<A NAME="RU22205ST-10">10</A> Hashimoto S. J. Chem. Soc., Chem. Commun. 1989, 685

<A NAME="RU22205ST-11">11</A> Ferrier RJ. Carbohydr. Res. 1973, 27: 55

<A NAME="RU22205ST-12">12</A> Fraser-Reid B. Pure Appl. Chem. 1993, 65: 779

<A NAME="RU22205ST-13">13</A> Blanchard JS. Annu. Rev. Biochem. 1995, 64: 29

<A NAME="RU22205ST-14">14</A> Lee RE. Brennan PJ. Besra GS. Glycobiology 1997, 7: 1121

<A NAME="RU22205ST-15A">15a</A> Besra GS. Khoo K.-H. McNeil MR. Dell A. Moeeis HR. Brennan PJ. Biochemistry 1995, 34: 4257

<A NAME="RU22205ST-15B">15b</A> Wolika BA. McNeil MR. de Hoffman E. Chojnacki T. Brennan PJ. J. Biol. Chem. 1994, 269: 23328

<A NAME="RU22205ST-15C">15c</A> McNeil MR. Daffe M. Brennan PJ. J. Biol. Chem. 1990, 265: 18200

<A NAME="RU22205ST-15D">15d</A> Daffe M. Brennan PJ. McNeil MR. J. Biol. Chem. 1990, 265: 6734

<A NAME="RU22205ST-15E">15e</A> McNeil MR. Robuck KG. Harter M. Brennan PJ. Glycobiology 1994, 4: 165

<A NAME="RU22205ST-16A">16a</A> Lee RE. Mikuová K. Brennan PJ. Besra GS. J. Am. Chem. Soc. 1995, 117: 11829

<A NAME="RU22205ST-16B">16b</A> Deng L. Mikuová K. Robuck KG. Scherman M. Brennan PJ. McNeil MR. Antimicrob. Agents Chemother. 1995, 39: 694

<A NAME="RU22205ST-17A">17a</A> Gurjar MK. Hotha S. Mereyala HB. Chem. Commun. 1998, 685

<A NAME="RU22205ST-17B">17b</A> D’Souza FW. Lowary TL. Org. Lett. 2000, 2: 1493

<A NAME="RU22205ST-17C">17c</A> D’Souza FW. Ayers JD. McCarren PR. Lowary TL. J. Am. Chem. Soc. 2000, 122: 1251

<A NAME="RU22205ST-17D">17d</A> Sanchez S. Bamhoud T. Prandi J. Tetrahedron Lett. 2000, 41: 7447

<A NAME="RU22205ST-17E">17e</A> Gurjar MK. Reddy LK. Hotha S. Org. Lett. 2001, 3: 321

<A NAME="RU22205ST-17F">17f</A> Gurjar MK. Reddy LK. Hotha S. J. Org. Chem. 2001, 66: 4657

<A NAME="RU22205ST-17G">17g</A> Han J. Gadikota RR. McCarren PR. Lowary TL. Carbohydr. Res. 2003, 338: 581

<A NAME="RU22205ST-18">18</A> Du Y. Pan Q. Kong F. Carbohydr. Res. 2000, 323: 28

<A NAME="RU22205ST-19">19</A> Izumi M. Tsuruta O. Hashimoto H. Carbohydr. Res. 1996, 280: 287

<A NAME="RU22205ST-20">20</A> Ding X. Wang W. Kong F. Carbohydr. Res. 1997, 303: 445

<A NAME="RU22205ST-21">21</A> Zeng Y. Li A. Kong F. Tetrahedron Lett. 2003, 44: 8325

<A NAME="RU22205ST-22">22</A> Mizutani K. Kasai R. Nakamura M. Tanaka O. Matsuura H. Carbohydr. Res. 1989, 185: 27

All new compounds gave satisfactory elemental analysis results. Selected physical data for some key compounds are as follows:
For 14: [α]_D +80.9 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.73 (s, 1 H, CNHCCl₃), 8.13-7.26 (m, 10 H, 2 × PhH), 6.64 (s, 1 H, H-1), 5.78 (d, 1 H, J _2,3 = 1.1 Hz, H-2), 5.51 (dd, 1 H, J _2,3 = 1.1 Hz, J _3,4 = 3.3 Hz, H-3), 4.68 (m, 1 H, H-4), 4.58 (dd, 1 H, J _4,5a = 4.2 Hz, J _5a,5b = 11.9 Hz, H-5a), 4.44 (dd, 1 H, J _4,5b = 5.51 Hz, J _5a,5b = 11.9 Hz, H-5b), 2.04 (s, 3 H, CH ₃CO). Anal. Calcd for C₂₄H₂₂Cl₃NO₈: C, 51.59; H, 3.97. Found: C, 51.74; H, 3.86.
For 16: [α]_D +98.1 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.09-7.26 (m, 10 H, 2 × PhH), 5.52 (d, 1 H, J _2,3 = 1.2 Hz, H-2), 5.42 (m, 1 H, H-3), 5.24 (s, 1 H, H-1), 4.31 (m, 1 H, H-4), 4.02-3.97 (m, 2 H, CH ₂C₁₁H₂₃), 3.75 (m, 1 H, 5a), 3.53 (m, 1 H, 5b), 1.65-0.82 (m, 23 H, CH₂C₁₁ H ₂₃). Anal. Calcd for C₃₂H₄₄O₇: C, 71.08; H, 8.20. Found: C, 71.44; H, 8.06.
For 18: [α]_D +101.1 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.14-7.26 (m, 15 H, 3 × PhH), 5.80 (s, 1 H, H-1), 5.74 (d, 1 H, J _2,3 = 1.4 Hz, H-2), 5.55 (d, 1 H, J _3,4 = 4.6 Hz, H-3), 4.59 (m, 1 H, H-4), 4.04 (m, 2 H, H-5a,b). Anal. Calcd for C₂₆H₂₄O₆S: C, 67.22; H, 5.21. Found: C, 67.04; H, 5.06.
For 20: [α]_D +44.7 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.06-7.26 (m, 15 H, 3 × PhH), 5.96 (d, 1 H, J _3,4 = 4.1 Hz, H-3), 5.61 (d, 1 H, J = 4.6 Hz, H-2), 5.50 (d, 1 H, J = 1.2 Hz, H-1), 5.45 (s, 1 H, H-1), 4.81 (dd, 1 H, J = 3.7, 11.9 Hz, H-5), 4.74 (d, 1 H, J = 3.9 Hz, H-3), 4.68 (dd, 1 H, J = 4.7, 11.9 Hz, H-5), 4.58 (m, 1 H, H-5), 4.35 (d, 1 H, J = 3.2 Hz, H-2), 4.24 (m, 1 H, H-4), 3.80 (m, 2 H, H-4, H-5), 1.53, 1.34 (2 s, 6 H, 2 CH ₃). Anal. Calcd for C₃₅H₃₈O₁₂: C, 64.61; H, 5.89. Found: C, 64.50; H, 5.74.
For 21: [α]_D +21.9 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.06-7.26 (m, 25 H, 5 × PhH), 5.94 (d, 1 H, H-1), 5.59 (d, 1 H, J = 4.8 Hz, H-3), 5.50 (d, 1 H, J = 1.1 Hz, H-2), 5.45 (d, 1 H, J = 1.2 Hz, H-2), 5.38 (d, 1 H, J = 4.1 Hz, H-3), 5.31 (s, 1 H, H-1), 5.27 (s, 1 H, H-1), 4.72-4.51 (m, 6 H, H-2, H-4, 4 × H-5), 4.46 (d, 1 H, J = 3.5 Hz, H-3), 4.36 (m, 1 H, H-4), 4.28 (m, 1 H, H-4), 4.04 (dd, 1 H, J = 5.4, 10.4 Hz, H-5), 3.75 (dd, 1 H, J = 4.6, 10.4 Hz, H-5), 2.02 (s, 3 H, CH ₃CO), 1.56, 1.34 [2 s, 6 H, C(CH ₃)₂]. Anal. Calcd for C₅₇H₅₈O₁₉: C, 65.38; H, 5.58. Found: C, 65.49; H, 5.41.
For 25: [α]_D +34.4 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.56 (s, 1 H, CNHCCl₃), 8.04-7.26 (m, 25 H, 5 × PhH), 6.37 (s, 1 H, H-1), 5.58 (d, 1 H, J = 4.8 Hz, H-3), 5.54 (d, 1 H, J = 1.1 Hz, H-2), 5.49 (d, 1 H, J = 1.2 Hz, H-2), 5.37 (d, 1 H, J = 4.1 Hz, H-3), 5.30 (s, 1 H, H-1), 5.28 (m, 1 H, H-2), 5.24 (s, 1 H, H-1), 4.76-4.50 (m, 6 H, H-3, H-4, 4 × H-5), 4.34 (m, 1 H, H-4), 4.11 (m, 1 H, H-4), 3.90 (dd, 1 H, J = 5.1, 10.4 Hz, H-5), 3.80 (dd, 1 H, J = 4.8, 10.4 Hz, H-5), 2.02, 2.00 (2 s, 6 H, 2 × CH ₃CO). Anal. Calcd for C₅₉H₅₆Cl₃NO₂₀: C, 58.79; H, 4.68. Found: C, 59.88; H, 5.24.
For 26: [α]_D +20.1 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.04-7.26 (m, 40 H, 8 × PhH), 5.80 (s, 1 H, H-1), 5.72 (d, 1 H, J = 4.1 Hz, H-3), 5.61 (m, 1 H, H-2), 5.53 (d, 1 H, J = 1.1 Hz, H-2), 5.47-5.45 (m, 3 H, H-1, H-2, H-3), 5.37 (s, 1 H, H-1), 5.34 (d, 1 H, J = 3.7 Hz, H-3), 5.27 (d, 1 H, J = 1.2 Hz, H-2), 5.21 (s, 1 H, H-1), 4.74 (dd, 1 H, J = 3.5, 11.9 Hz, H-5), 4.65-4.33 (m, 8 H, H-3, 4 H-4, 3 × H-5), 4.18 (dd, 1 H, J = 4.0, 11.9 Hz, H-5), 4.05 (dd, 1 H, J = 4.1, 11.9 Hz, H-5), 3.88 (m, 2 H, 2 × H-5), 2.01, 1.97 (2 × s, 6 H, 2 × CH ₃CO). ¹³C NMR (100 MHz, CDCl₃): δ = 170.60, 169.94 (2 × CH₃ CO), 165.96, 165.63, 165.57, 165.35, 165.31, 164.96, 164.91 (7 × PhCO), 105.97, 105.69, 105.46, 91.09 (4 × C-1), 20.68, 20.67 (2 × CH₃CO). Anal. Calcd for C₈₃H₇₈O₂₅S: C, 66.13; H, 5.22. Found: C, 66.41; H, 5.04.
For 27: [α]_D +69.4 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.03-7.22 (m, 35 H, 7 × PhH), 5.59 (d, 1 H, J = 4.6 Hz, H-3), 5.53 (d, 1 H, H-2), 5.48 (s, 1 H, H-1), 5.46 (d, 1 H, J = 4.6 Hz, H-3), 5.44 (d, 1 H, J = 1.2 Hz, H-2), 5.41 (d, 1 H, J = 1.1 Hz, H-2), 5.37 (s, 1 H, H-1), 5.34 (d, 1 H, J = 3.4 Hz, H-3), 5.28 (d, 1 H, J = 1.3 Hz, H-2), 5.21 (d, 2 H, J = 4.7 Hz, 2 × H-1), 4.73 (dd, 1 H, J = 3.6, 11.6 Hz, H-5), 4.63 (m, 1 H, H-5), 4.53-4.33 (m, 7 H, H-3, 2 × H-4, 2 × H-5, CH ₂C₁₁H₂₃), 4.13 (m, 1 H, H-5), 4.05 (dd, 1 H, J = 3.9, 11.6 Hz, H-5), 3.91 (dd, 1 H, J = 3.1, 11.6 Hz, H-5), 3.83 (dd, 1 H, J = 2.8, 11.9 Hz, H-5), 3.74 (m, 1 H, H-4), 3.49 (m,1 H, H-4), 2.00, 1.98 (2 × s, 6 H, 2 × CH ₃CO), 1.61-0.82 (m, 23 H, CH₂C₁₁ H ₂₃). Anal. Calcd for C₈₉H₉₈O₂₆: C, 67.50; H, 6.24. Found: C, 67.66; H, 6.09.
For 28: [α]_D +74.4 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.04-7.26 (m, 35 H, 7 × PhH), 5.60 (d, 1 H, J = 4.6 Hz, H-3), 5.57 (d, 1 H, J = 1.3 Hz, H-2), 5.4 (m, 2 H, H-1, H-3), 5.43 (d, 1 H, J = 1.2 Hz, H-2), 5.40 (d, 1 H, J = 1.1 Hz, H-2), 5.35 (m, 2 H, H-1, H-3), 5.29 (d, 1 H, 1.4 Hz, H-2), 5.22 (s, 1 H, H-1), 5.21 (s, 1 H, H-1), 4.78 (dd, 1 H, J = 3.6, 11.9 Hz, H-5), 4.65 (dd, 1 H, J = 4.6, 11.9 Hz, H-5), 4.59 (m, 1 H, H-4), 4.50 (m, 1 H, H-4), 4.38-4.32 (m, 3 H, H-3, 2 × H-5), 4.16 (dd, 1 H, J = 4.3, 11.2 Hz, H-5), 3.99-3.92 (m, 4 H, 2 × H-5, CH ₂C₁₁H₂₃), 3.84 (dd, 1 H, J = 3.5, 11.2 Hz, H-5), 3.74 (m, 1 H, H-4), 3.50 (m,1 H, H-4), 2.00 (s, H, CH₃CO), 1.60-0.86 (m, 23 H, CH₂C₁₁ H ₂₃). ¹³C NMR (100 MHz, CDCl₃): δ = 169.92 (CH₃ CO), 166.16, 165.90, 165.67, 165.54, 165.42, 165.01, 164.86 (7 × PhCO), 105.74, 105.46, 105.41, 105.42 (4 × C-1), 20.67 (CH₃CO). Anal. Calcd for C₈₇H₉₆O₂₅: C, 67.78; H, 6.28. Found: C, 67.60; H, 6.41.
For 29: [α]_D +69.4 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 8.01-7.26 (m, 70 H, 14 × PhH), 5.51 (s, H-1), 5.50 (s, H-1), 5.45-5.40 (m, 3 H, H-1), 5.33 (s, H-1), 5.45-5.40 (m, 2 H, H-1), 1.99, 1.97, 1.95 (3 × s, 9 H, 3 × CH ₃CO), 1.57-0.85 (m, 23 H, CH₂C₁₁ H ₂₃). ¹³C NMR (100 MHz, CDCl₃): δ = 170.58, 169.98, 169.91 (3 × CH₃ CO), 165.93, 169.94, 165.62, 165.63, 165.55, 165.51, 165.49, 165.41, 165.42, 165.12, 165.04, 164.93, 164.88, 164.84 (14 × PhCO), 106.03, 105.92, 105.79, 105.61, 105.59, 105.52, 105.47, 105.42 (8 × C-1), 20.70, 20.69, 20.66 (3 × CH₃CO). Anal. Calcd for C₁₆₄H₁₆₈O₅₀: C, 67.02; H, 5.76. Found: C, 67.11; H, 5.60.
For 6: [α]_D -18.9 (c 1.0, H₂O). ¹H NMR (400 MHz, D₂O): δ = 5.16 (s, 2 H, H-1), 5.10 (s, 5 H, H-1), 4.96 (s, 1 H, H-1). 1.62-0.90 (m, 23 H, CH₂C₁₁ H ₂₃). ¹³C NMR (100 MHz, CDCl₃): δ = 107.66, 107.61, 107.59, 107.55, 107.52, 107.43, 107.25, 107.18 (8 × C-1). MALDI-TOF MS: m/z calcd for C₆₀H₁₀₆O₃₃: 1355.46 [M], found: 1378.09 [M + Na]⁺.