Solid-Phase Synthesis and Combinatorial Technologies
.pdf
9.5 APPLICATIONS TO MOLECULAR RECOGNITION 493
|
O |
|
|
blue |
HN |
|
|
dye |
O |
|
|
|
O |
|
N |
|
N |
|
|
|
H |
O |
COOPfp |
|
O |
9.144a
O2N
red |
N |
dye |
N |
|
O |
|
N |
N |
|
|
O |
O |
COOPfp |
9.144b
O O
M3
L 
NH
N M
H 2
HN 
M1
O
L38
60-member encoded pool library
M1 Gly, L- and D- Val, L- and D-Pro, L- and D-Phe,
|
L- and D-Asn(Trt), L- and D-His (Trt), |
|
|
|
|
L- and D-Asp(OtBu), L- and D-Ser(OtBu); |
O |
|
|
O |
|
|
all N-Fmoc protected. |
|
N |
||
|
|
|
|
N |
|
|
|
|
|
H |
H |
|
M3 |
PfpOOC |
|
|
|
|
|
|
|
H |
H |
M |
NH2 |
|
|
N |
N |
|
|
|
|
||
2 |
|
O |
|
|
O |
|
N |
|
|
||
|
|
|
|
|
|
|
NHBoc |
|
|
|
|
M2,1: |
RR enantiomer |
M |
: |
RRRR enantiomer |
|
M2,2: |
SS enantiomer |
3,1 |
|
|
|
M |
: |
SSSS enantiomer |
|||
|
|
3,2 |
|
|
|
Figure 9.55 Structure of the SP peptidomimetic encoded pool chiral selector libraryL38 and of the monomer sets M1–M3 used for its synthesis.
494 APPLICATIONS OF SYNTHETIC LIBRARIES
|
N |
a-c |
N |
|
a,b |
N |
M2,1: |
RR enantiomer |
|
|
|
|
|
M2,2: |
SS enantiomer |
||
|
|
|
|
|
|
|
||
N3 |
N3 |
|
N3 |
NHBoc |
H N |
|
NHBoc |
|
|
9.145 |
|
|
|
2 |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
a: Ph3P, toluene, reflux, 1 hr; b: water/THF, reflux, 1 hr; c: Boc2O, DCM, rt, 16 hrs. |
||||||
|
|
|
|
|
O |
|
O |
|
|
NH2 |
d |
NH2 |
e,f |
|
NH |
HN |
|
|
NH2 |
|
NHBoc |
|
NH3+ |
NH3+ |
|
|
|
|
O |
|
O |
|
|
|
|
|
|
N |
N |
|
M3,1: |
RRRR enantiomer |
|
|
g,h,i |
|
H |
H |
|
M3,2: |
SSSS enantiomer |
|
|
PfpOOC |
|
|
|
|
||||
|
|
|
|
|
|
|
|
|
|
|
H |
H |
|
d: Boc-on, DMSO, rt, 16 hrs; e: isophthaloyl |
|||
|
|
N |
N |
|
chloride, TEA, DCM, rt, 4 hrs; f: TFA, DCM, rt, |
|||
|
|
O |
|
O |
1 hr; g: bis-Pfp,mono-Me ester of trimesic acid, |
|||
|
|
|
|
DIPEA, THF, rt, 16 hrs; h: NaOH, water, MeOH, |
||||
THF, rt, 4 hrs; i: PfpOH, EDC, DCM, rt, 16 hrs.
Figure 9.56 Synthesis of the monomer sets M2–M3 used for the synthesis of the SP peptidomimetic encoded pool chiral selector library L38.
elaborated to give four Boc-protected isomeric constructs 9.146a–d (steps a–c, Fig. 9.57). The library L38 was then prepared as shown in Fig. 9.58. Aminomethyl PS resin was acylated with an Fmoc-protected amino acid linker (step a), and after Fmoc deprotection (step b) the resin was divided into four aliquots and treated with four tags, according to a popular encoding method (step c) (177). The portions of encoded resin were then acylated with 9.146a–d to give the four encoded discretes 9.147a–d (step d), and, after pooling, the resin was deprotected, split into 15 aliquots, and tagged (steps e and f). Finally, the encoded intermediates were acylated with M1, pooled, and deprotected (steps g and b, Fig. 9.58) to give the encoded library L38.
The library was screened simply by incubating an excess of 9.144a,b (equimolar amounts of the two colored enantiomers) with a library aliquot in chloroform for 4 h. The library was then washed and dried and finally observed with a microscope to determine the color of each bead. The most selective beads showed either blue
REFERENCES 497
T2 |
|
|
|
|
|
T1 |
H |
|
|
O |
O |
|
L N |
|
|
N |
N |
|
O |
|
O |
H |
H |
|
|
|
|
||
|
O |
|
|
|
|
|
|
N |
|
|
|
|
|
|
|
|
|
|
|
|
N |
|
|
|
|
|
H |
H |
H |
|
|
|
|
N |
N |
|
|
|
NH |
O |
O |
|
|
|
O |
|
|
H2NOC
NH2
9.148a
D-Asn-RR-RRRR 81% selection for
9.144a
9.148a other enantiomer L-Asn-SS-SSSS 73% selection for
9.144b
Figure 9.59 Chiral selectors individuated from screening of the SP peptidomimetic encoded pool chiral selector library L38: compounds 9.148a and 9.148b.
REFERENCES
1.Persidis, A., in Combinatorial Chemistry and Combinatorial Technologies: Methods and Applications, S. Miertus and G. Fassina (Eds.). Marcel Dekker, Inc., New York, 1999, pp. 405–422.
2.Tucker, G. T., J. Pharm. Pharmacol. 46, 417–424 (1994).
3.Heward, J. and Gough, S. C. L., Clin. Sci. 93, 479–491 (1997).
4.Pirtle, R. M. and Pirtle, I. L., in Transfer RNA in Protein Synthesis, D. L. Hatfield, B. J. Lee and R. M. Pirtle (Eds.). CRC, Boca Raton, FL, 1992, pp. 141–155.
5.Liang, P., Wang, F., Zhu, W., O’Connell, R. P. and Averboukh, L.,Methods Mol. Med. 13, 3–13 (1998).
6.Anderson, N. L. and Anderson, N. G., Electrophoresis 19, 1853–1861 (1998).
7.Stubberfield, C. R. and Page, M. J., Expert Opin. Invest. Drugs 8, 65–70 (1999).
8.Andrade, M. A. and Sander, C., Curr. Opin. Biotechnol. 8, 675–683 (1997).
9.Smith, T. F., Trends Genet. 14, 291–293 (1998).
10.Koonin, E. V., Tatusov, R. L. and Galperin, M. Y., Curr. Opin. Struct. Biol. 8, 355–363 (1998).
11.Schena, M., Heller, R. A., Theriault, T. P., Konrad, K., Lachenmeier, E. and Davis, R. W.,
Trends Biotechnol. 16, 301–306 (1998).
12.Thakker, R. V., Princ. Bone Biol., 837–851 (1996).
498APPLICATIONS OF SYNTHETIC LIBRARIES
13.Guerre-Millo, M., Biomed. Pharmacother. 51, 318–323 (1997).
14.Van Cott, K. E. and Velander, W. H., Expert Opin. Invest. Drugs 7, 1683–1690 (1998).
15.Heddle, J. A., Environ. Mol. Mutagen. 32, 110–114 (1998).
16.Schreiber, S. L., Bioorg. Med. Chem. 6, 1127–1152 (1998).
17.Crews, C. M. and Splittgerber, U., Trends Biol. Sci. 24, 317–320 (1999).
18.http://www-schreiber.chem.harvard.edu/
19.Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. L. and Mitchison,
T.J., Science 286, 971–974 (1999).
20.Stockwell, B. R., Haggarty, S. J. and Schreiber, S. L., Chem. Biol. 6, 71–83 (1999).
21.Hagan, I. and Yanagida, M., Nature 356, 74–76 (1992).
22.Blangy, A., Lane, H. A., d’Herin, P., Harper, M., Kress, M. and Nigg, E. A., Cell 83, 1159–1169 (1995).
23.Sawin, K. E., Nature 359, 540–542 (1992).
24.Stockwell, B. R., Hardwick, J. S., Tong, J. K. and Schreiber, S. L.,J. Am. Chem. Soc. 121, 10662–10663 (1999).
25.Carcamo, J., Zentella, A. and Massague, J., Mol. Cell. Biol. 15, 1573–1581 (1995).
26.Zhao, H. and Eide, D., Proc. Natl. Acad. Sci. USA 93, 2454–2458 (1996).
27.Askwith, C., Eide, D., Van Ho, A., Bernard, P. S., Li, L., Davis-Kaplan, S., Sipe, D. M. and Kaplan, J., Cell 76, 403–410 (1994).
28.Varela, J. C., van Beekvelt, C., Planta, R. J. and Mager, W. H., Mol. Microbiol. 6, 2183–2190 (1992).
29.Mattheakis, L. C., Olivan, S. E., Dias, J. M. and Horthrop, J. P., Chem. Biol. 6, 835–844 (1999).
30.Sarwar Nasir, M. and Jolley, M. E., Comb. Chem. High Throughput Screening 2, 177–190 (1999).
31.Zuck, P., Lao, Z., Skwish, S., Glickman, J. F., Yang, K., Burbaum, J. and Inglese, J.,Proc. Natl. Acad. Sci. USA 96, 11122–11127 (1999).
32.Beutel, B. A., in Combinatorial Chemistry and Molecular Diversity in Drug Discovery
E.M. Gordon and J. Kerwin (Eds.). Wiley-Liss, New York, 1998, pp. 421–432.
33.Hill, D. C., Curr. Opin. Drug Discovery Dev . 1, 92–97 (1998).
34.Fernandes, P. B., Curr. Opin. Chem. Biol. 2, 597–603 (1998).
35.Kenny, B. A., Bushfield, M., Parry-Smith, D. J., Fogarty, S. and Treherne, J. M., Prog. Drug Res. 51, 245–269 (1998).
36.Venton, D. L. and Woodbury, C. P., Chemometr. Intell. Lab. Systems 48, 131–150 (1999).
37.Fox, S., Farr-Jones, S. and Yund, M. A., J. Biomol. Screen. 4, 183–186 (1999).
38.Carrano, L. and Donadio, S., in Combinatorial Chemistry and Combinatorial Technolo - gies: Methods and Applications , S. Miertus and G. Fassina (Eds.). Marcel Dekker, Inc., New York, 1999, pp. 233–250.
39.Hann, M., Hudson, B., Lewell, X., Lifely, R., Miller, L. and Ramsden, N., J. Chem. Inf. Comput. Sci. 39, 897–902 (1999).
40.Leland, B. A., J. Chem. Inf. Comput. Sci. 37, 62–70 (1997).
41.Muskal, S. M., in A Practical Guide to Combinatorial Chemistry, A. W. Czarnik and S.
H.Dewitt (Eds.). ACS, Washington, DC, 1997, pp. 357–397.
REFERENCES 499
42.Bauer, B. E., in High Throughput Screening, J. P. Devlin (Ed.). Marcel Dekker, Inc., New York, 1997, pp. 551–581.
43.Weininger, D., in Combinatorial Chemistry and Molecular Diversity in Drug Discovery ,
E.M. Gordon and J. Kerwin (Eds.). Wiley-Liss, New York, 1998, pp. 483–498.
44.Heuer, K. I., Med. Res. Rev. 19, 209–221 (1999).
45.Lee, M. S., Nakanishi, H. and Kahn, M., Curr. Opin. Drug Discovery Dev. 2, 332–341 (1999).
46.Kuzniar, E., Comb. Chem. High Throughput Screening 2, 237–245 (1999).
47.Powers, D. G., Casebier, D. S., Fokas, D., Ryan, W. J., Troth, J. R. and Coffen, D. L., Tetrahedron 54, 4085–4096 (1998).
48.Ostresh, J. M., Husar, G. M., Blondelle, S., Dorner, B., Weber, P. A. and Houghten, R. A.,
Proc. Natl. Acad. Sci. USA 91, 11138–11142 (1994).
49.Newton, C. G., Exp. Opin. Ther. Patents 6, 827–835 (1996).
50.Bozicevic, K., Annu. Rep. Combi. Chem. Mol. Diversity 1, 298–313 (1997).
51.Newton, C. G., Exp. Opin. Ther. Patents 7, 1183–1194 (1997).
52.Green, G. D., Mol. Diversity 3, 247–252 (1998).
53.Jakobsen, P. H., Kurtzhals, P. and Poulsen, F., Exp. Opin. Ther. Patents 8, 1157–1165 (1998).
54.Mulligan, L. and Steele, P., Exp. Opin. Ther. Patents 9, 507–514 (1999).
55.Harper, M. F. and Newton, C. G., Exp. Opin. Ther. Patents 9, 583–624 (1999).
56.Bhandari, A., Jones, D. G., Schullek, J. R., Vo, K., Schunk, C. A., Tamanaha, L. L., Chen, D., Yuan, Z., Needels, M. C. and Gallop, M. A., Bioorg. Med. Chem. Lett. 8, 2303–2308 (1998).
57.Thomas, J. B., Fall, M. J., Cooper, J. B., Rothman, R. B., Mascarella, S. W., Xu, H., Partilla,
J.S., Dersch, C. M., McCullough, K. B., Cantrell, B. E., Zimmerman, D. M. and Carroll,
F.I., J. Med. Chem. 41, 5188–5197 (1998).
58.Thomas, J. B., Mascarella, S. W., Rothman, R. B., Partilla, J. S., Xu, H., McCullough, K. B., Dersch, C. M., Cantrell, B. E., Zimmerman, D. M. and Carroll, F. I., J. Med. Chem. 41, 1980–1990 (1998).
59.Mitch, C. H., Leander, J. D., Mendelsohn, L. G., Shaw, W. N., Wong, D. T., Cantrell, B. E., Johnson, B. G., Reel, J. K., Snoddy, J. D. et al., J. Med. Chem. 36, 2842–2850 (1993).
60.Harre, M., Nickisch, K. and Tilstam, U., React. Funct. Polym. 41, 111–114 (1999).
61.Raillard, S. P., Ji, G., Mann, A. D. and Baer, T. A.,Org. Proc. Res. Dev. 3, 177–183 (1999).
62.Edwards, P. J., Gardner, M., Klute, W., Smith, G. F. and Terrett, N. K., Curr. Opin. Drug Discovery Dev. 2, 321–331 (1999).
63.Harre, M., Tilstam, U. and Weinmann, H., Org. Proc. Res. Dev. 3, 304–318 (1999).
64.Berman, J., Halm, K., Adkison, K. and Shaffer, J., J. Med. Chem. 40, 827–829 (1997).
65.Olah, T. V., Mcloughlin, D. A. and Gilbert, J. D., Rapid Commun. Mass Spectrom. 11, 17–23 (1997).
66.Kuo, B.-S., Van Noord, T., Feng, M. R. and Wright, D. S., J. Pharm. Biomed. Anal. 16, 837–846 (1998).
67.Frick, L. W., Higton, D. M., Wring, S. A. and Wells-Knecht, K. J., Med. Chem. Res. 8, 472–477 (1998).
500APPLICATIONS OF SYNTHETIC LIBRARIES
68.Corcoran, O., Nicholson, J. K. and Wilson, I. D., Anal. Commun. 36, 259–261 (1999).
69.Atherton, J. P., Van Noord, T. J. and Kuo, B.-S.,J. Pharm. Biomed. Anal. 20, 39–47 (1999).
70.Beaudry, F., Le Blanc, J. C. Y., Coutu, M. and Brown, N. K., Rapid Commun. Mass. Spectrom. 12, 1216–1222 (1998).
71.Bayliss, M. K. and Frick, L. W., Curr. Opin. Drug Discovery Dev . 2, 20–25 (1999).
72.Tarbit, M. H. and Berman, J., Curr. Opin. Chem. Biol. 2, 411–416 (1998).
73.Mandagere, A. K., Correll, M. A., Mooney, J. P., Poole, J. C., Hwang, K.-K. and Cheng,
L.K., Pharmaceut. Res. 13, S237 (1996).
74.Rubas, W., Cromwell, M. E. M., Mrsny, R. J., Ingle, G. and Elias, K. A.,Pharmaceut. Res. 13, 23–26 (1996).
75.Kansy, M., Senner, F. and Gubernator, K., J. Med. Chem. 41, 1007–1010 (1998).
76.Taylor, E. W., Gibbons, J. A. and Braeckman, R. A.,Pharmaceut. Res. 14, 572–577 (1997).
77.Stevenson, C. L., Augustijns, P. F. and Hendren, R. W.,Int. J. Pharmaceut. 177, 103–115 (1999).
78.Lim, H. K., Stellingweif, S., Sisenwine, S. and Chan, K. W.,J. Chromatog. A 831, 227–241 (1999).
79.Li, A. P., Gorycki, P. D., Hengstler, J. G., Kedderis, G. L., Koebe, H. G., Rahmani, R., de Sousas, G., Silva, J. M. and Skett, P., Chem.-Biol. Interact. 121, 17–35 (1999).
80.Caldwell, G. W., Masucci, J. A. and Chacon, E.,Comb. Chem. High Throughput Screening 2, 39–51 (1999).
81.Crespi, C. L., Miller, V. P. and Penman, B. W., Anal. Biochem. 248, 188–190 (1997).
82.Crespi, C. L., Miller, V. P. and Penman, B. W., Med. Chem. Res. 8, 457–471 (1998).
83.Onderwater, R. C. A., Venhorst, J., Commandeur, J. N. M. and Vermeulen, N. P. E.,Chem. Res. Toxicol. 12, 555–559 (1999).
84.Van Breemen, R. B., Nikolic, B. and Bolton, J. L.,Drug Metab. Dispos. 26, 85–90 (1998).
85.Gibbons, J. A., Taylor, E. W. and Braeckman, R. A., in Combinatorial Chemistry and Molecular Diversity in Drug Discovery , E. M. Gordon and J. Kerwin (Eds.). Wiley-Liss, New York, 1998, pp. 453–474.
86.Rodrigues, A. D., Pharmaceut. Res. 14, 1504–1510 (1997).
87.Rodrigues, A. D., Med. Chem. Res. 8, 422–433 (1998).
88.Smith, D. A. and Van der Waterbeemd, H., Curr. Opin. Chem. Biol. 3, 373–378 (1999).
89.Darvas, F. and Dorman, G., Chim. Oggi 17, 10–13 (1999).
90.Watt, A. P., Morrison, D. and Evans, D. C., Drug Disc. Today 5, 17–24 (2000).
91.Spraul, M., Hofmann, M., Ackermann, M., Nicholls, A. W., Damment, S., J. P., Haselden,
J.N., Shockcor, J. P., Nicholson, J. K. and Lindon, J. C., Analyst 122, 339–341 (1997).
92.Afshari, C. A., Nuwaysir, E. F. and Barrett, J. C., Cancer Res. 59, 4759–4760 (1999).
93.Todd, M. D., Lin, X., Stankowski, L. F. Jr., Desai, M. and Wolfgang, G. H. I., J. Biomol. Screen. 4, 259–268 (1999).
94.Shapiro, M. A., Sesnie, J. C., Joannides, E. T., Malta, T. E., Dever, J. A. and Heifetz, C. L., J. Pharmacol. Toxicol. Methods 36, 185–187 (1996).
95.Cronin, M. T., Pharm. Pharmacol. Commun. 4, 157–163 (1998).
96.Wang, J., Lai, L. and Tang, Y., J. Chem. Inf. Comput. Sci. 39, 1173–1189 (1999).
97.Kramer, P. J., J. Pharm. Pharmacol. 50, 395–405 (1998).
REFERENCES 501
98.Gibson, G. G., Biomed. Health Res. 25, 13–23 (1998).
99.Johnson, D. E., Braeckman, R. A. and Wolfgang, G. H.,Curr. Opin. Drug Discovery Dev. 2, 49–57 (1999).
100.Todd, M. D. and Ulrich, R. G., Curr. Opin. Drug Discovery Dev. 2, 58–68 (1999).
101.Lipinski, C. A., Bissett, B. D., Campos, G. andy Feeney, P. J., Book of Abstracts, MEDI-161. 217th ACS, Washington, DC Anaheim, CA, March 21st–25th 1999.
102.Chen, H.-W. and Fang, Z.-L., Anal. Chim. Acta 376, 209–220 (1998).
103.Valko, K., Bevan, C. and Reynolds, D., Anal. Chem. 69, 2022–2029 (1997).
104.Clark, D. E., J. Pharm. Sci. 88, 815–821 (1999).
105.Lipinski, C. A., Lombardo, F., Dominy, B. W. and Feeney, P. J., Adv. Drug Delivery Rev. 23, 3–25 (1997).
106.Wong, D. W. S., Robertson, G. H., Tillin, S. J. and Wong, C., J. Agric. Food Chem. 46, 3852–3857 (1998).
107.Reed, J. D., Edwards, D. L. and Gonzales, C. F.,Mol. Plant-Microbe Interact. 10, 537–549 (1997).
108.Mee, R. P., Auton, T. R., Eldridge, M. D. and Brooks, A. G.,Pestic. Sci. 51, 91–92 (1997).
109.Lyga, J. W., Ali, S. F., Webster, C. A., Simmons, K. A., Plummer, J. and Galietti, M. E.,
Electron. Conf. Heterocycl. Chem. Proc . (1997).
110.Ridley, S. M., Elliott, A. C., Yeung, M. and Youle, D., Pestic. Sci. 54, 327–337 (1998).
111.Corran, A. J., Renwick, A. and Dunbar, S. J., Pestic. Sci. 54, 338–344 (1998).
112.Jansson, R. K., Halliday, W. R. and Argentine, J. A., J. Econ. Entomol. 90, 1500–1507 (1997).
113.Petsko, G. A., Ringe, D. and Hogan, J., Spec. Publ.-R. Soc. Chem. 233, 66–70 (1999).
114.Khan, J. A., Gijs, L., Berger, C., Martin, N., Piraprez, G., Spinnler, H. E., Vulfson, E. N. and Collin, S., J. Agric. Food Chem. 47, 3269–3273 (1999).
115.Berger, C., Martin, N., Collin, S., Gijs, L., Khan, J. A., Piraprez, G., Spinnler, H. E. and Vulfson, E. N., J. Agric. Food Chem. 47, 3274–3279 (1999).
116.Wong, D. W. S. and Robertson, G. H., Adv. Exp. Med. Biol. 464, 91–105 (1999).
117.Strauss, C. R., Aust. J. Chem. 52, 83–96 (1999).
118.Parlow, J. J. and Normansell, J. E., Mol. Diversity 1, 266–269 (1996).
119.Pilipauskas, D. R., Med. Res. Rev. 19, 463–474 (1999).
120.Geysen, H. M., Wagner, C. D., Bodnar, W. M., Markworth, C. J., Parke, G. J., Schoenen, F. J., Wagner, D. S. and Kinder, D. S., Chem. Biol. 6, 679–688 (1996).
121.Warmus, J. S., Ryder, T. R., Hodges, J. C., Kennedy, R. M. and Brady, K. D.,Bioorg. Med. Chem. Lett. 8, 2309–2314 (1998).
122.Bray, A. M., Chiefari, D. S., Valerio, R. M. and Maeji, N. J., Tetrahedron Lett. 36, 5081–5084 (1995).
123.Gayo, L. M. and Suto, M. J., Tetrahedron Lett. 38, 513–516 (1997).
124.Kuo, P. Y., Du, H., Corkan, A., Yang, K. and Lindsey, J. S., Chemom. Intell. Lab. Systems 48, 219–234 (1999).
125.Hsu, L. C., Ping, L.-J., Webb, E. C. and Wrzosek, T. J., Lab. Robot. Autom. 11, 186–192 (1999).
502APPLICATIONS OF SYNTHETIC LIBRARIES
126.Lindsey, J. S., in A Practical Guide to Combinatorial Chemistry , A. W. Czarnik and S. H. DeWitt (Eds.). ACS, Washington, DC, 1997, pp. 309–326.
127.Liu, G. and Ellman, J. A., J. Org. Chem. 60, 7712–7713 (1995).
128.Burgess, K., Lim, H.-J., Porte, A. M. and Sulikowski, G. A.,Angew. Chem., Int. Ed. Engl. 35, 220–222 (1996).
129.Borman, S., Chem. Eng. News 74, 37–39 (1996).
130.Burgess, K. and Porte, A. M., Adv. Catalyt. Proc. 2, 69–82 (1997).
131.Weinberg, W. H., Jandeleit, B., Self, K. and Turner, H.,Curr. Opin. Solid State Mater. Sci. 3, 104–110 (1998).
132.Hoveyda, A. H., Chem. Biol. 5, R187–R191 (1998).
133.Jandeleit, B. and Weinberg, W. H., Chem. Ind., 795–798 (1998).
134.Jandeleit, B., Turner, H. W., Uno, T., Van Beek, J. A. M. and Weinberg, W. H.,CATTECH 2, 101–123 (1998).
135.Bein, T., Angew. Chem., Int. Ed. Engl. 38, 323–326 (1999).
136.Kuntz, K. W., Snapper, M. L. and Hoveyda, A. H., Curr. Opin. Chem. Biol. 3, 313–319 (1999).
137.Newsam, J. M. and Schuth, F., Biotech. Bioeng. 61, 203–216 (1999).
138.Doyle, M. P., Chem. Rev. 86, 919–940 (1986).
139.Lim, H.-J. and Sulikowski, G. A., J. Org. Chem. 60, 2326–2327 (1995).
140.Doyle, M. P., Dyatkin, A. B., Roos, G. H. P., Canas, F., Pierson, D. A., van Basten, A., Mueller, P. and Polleux, P., J. Am. Chem. Soc. 116, 4507–4508 (1994).
141.Lowenthal, R. E., Abiko, A. and Masamune, S.,Tetrahedron Lett. 31, 6005–6008 (1990).
142.Fritschi, H., Leutenegger, U., Siegmann, K., Pfaltz, A., Keller, W. and Krathy, C., Helv. Chim. Acta 71, 1541–1552 (1988).
143.Pfaltz, A., Acc. Chem. Res. 26, 339–345 (1993).
144.Jacobsen, E. N., Zhang, W., Muci, A. R., Ecker, J. R. and Deng, L., J. Am. Chem. Soc. 113, 7063–7064 (1991).
145.Cooper, A. C., J. Am. Chem. Soc. 120, 9971–9972 (1998).
146.Reetz, M. T., Becker, M. H., Kuhling, K. M. and Holzwarth, A., Angew. Chem., Int. Ed. Engl. 37, 2647–2650 (1998).
147.Sigman, M. S. and Jacobsen, E. N., J. Am. Chem. Soc. 120, 5315–5316 (1998).
148.Berg, T., Vandersteen, A. M. and Janda, K. D., Bioorg. Med. Chem. Lett. 8, 1221–1224 (1998).
149.Berg, T., Simeonov, A. and Janda, K. D., J. Comb. Chem. 1, 96–100 (1999).
150.Moye-Sherman, D., Welch, M. B., Reibenspies, J. and Burgess, K., Chem. Commun., 2377–2378 (1998).
151.Bromidge, S., Wilson, P. C. and Whiting, A., Tetrahedron Lett. 39, 8905–8908 (1998).
152.Huffman, M. A. and Reider, P. J., Tetrahedron Lett. 40, 831–834 (1999).
153.Reetz, M. T., Becker, M. H., Klein, H.-W. and Stockigt, D., Angew. Chem., Int. Ed. Engl. 38, 1758–1761 (1999).
154.Lavastre, O. and Morken, J. P., Angew. Chem., Int. Ed. Engl. 38, 3163–3165 (1999).
155.Shaughnessy, K. H., Kim, P. and Hartwig, J. F.,J. Am. Chem. Soc. 121, 2123–2132 (1999).