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Journal articles on the topic 'Hydroxyethylene isosters'

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Published: 11 March 2023

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1

JONES, D. M., B. NILSSON, and M. SZELKE. "ChemInform Abstract: A Short Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosters." ChemInform 24, no. 39 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199339146.

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2

D'ANIELLO, F., S. GEHANNE, and M. TADDEI. "ChemInform Abstract: A Convenient Approach to Hydroxyethylene Dipeptide Isosters Using Allylsilane Chemistry." ChemInform 24, no. 6 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199306274.

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3

GHOSH, A. K., S. P. MCKEE, and W. J. THOMPSON. "ChemInform Abstract: An Efficient Synthesis of Hydroxyethylene Dipeptide Isosters: The Core Unit of Potent HIV-1 Protease Inhibitors." ChemInform 23, no. 13 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199213295.

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4

ROSENBERG, S. H., S. A. BOYD, and R. A. MANTEI. "ChemInform Abstract: A Stereoselective Synthesis of Hydroxyethylene and erythro- Dihydroxyethylene Dipeptide Isosters: A Facial Selective anti-Aldol Reaction." ChemInform 23, no. 28 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199228054.

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5

Danielmeier, Karsten, Kerstin Schierle, and Eberhard Steckhan. "A New Chiral, Cationicβ-Amino Alcohol Equivalent: A Variable Approach to Enantiomerically Pure Building Blocks for Hydroxyethylene Isosters." Angewandte Chemie International Edition in English 35, no. 19 (October 18, 1996): 2247–48. http://dx.doi.org/10.1002/anie.199622471.

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6

Lindgren, Cecilia, Ida E. Andersson, Lotta Berg, Doreen Dobritzsch, Changrong Ge, Sabrina Haag, Urszula Uciechowska, Rikard Holmdahl, Jan Kihlberg, and Anna Linusson. "Hydroxyethylene isosteres introduced in type II collagen fragments substantially alter the structure and dynamics of class II MHC Aq/glycopeptide complexes." Organic & Biomolecular Chemistry 13, no. 22 (2015): 6203–16. http://dx.doi.org/10.1039/c5ob00395d.

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7

Marinier, Aime, Mihaly V. Toth, Kathryn Houseman, Richard Mueller, and Garland R. Marshall. "HIV-1 protease inhibitors: Ketomethylene isosteres with unusually high affinity compared with hydroxyethylene isostere analogs." Bioorganic & Medicinal Chemistry 2, no. 9 (September 1994): 919–25. http://dx.doi.org/10.1016/s0968-0896(00)82041-6.

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8

Boyd, Steven A., Robert A. Mantei, Chi Nung Hsiao, and William R. Baker. "Stereoselective syntheses of hydroxyethylene dipeptide isosteres." Journal of Organic Chemistry 56, no. 1 (January 1991): 438–42. http://dx.doi.org/10.1021/jo00001a083.

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9

KONIECZNY, M. T., P. H. TOMA, and M. CUSHMAN. "ChemInform Abstract: Synthesis of Hydroxyethylene Isosters of the Transition State of the HIV Protease-Catalyzed Phe-Pro Hydrolysis: Reaction of 2-((Boc)amino)- 1-(2′-oxocyclopentyl)-3-phenylpropanols with Diethyl Phosphorocyanidate and Lithium Cyanide Fo." ChemInform 24, no. 51 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199351192.

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10

Diederich, Ann M., and David M. Ryckman. "Stereoselective synthesis of a hydroxyethylene dipeptide isostere." Tetrahedron Letters 34, no. 39 (September 1993): 6169–72. http://dx.doi.org/10.1016/s0040-4039(00)73701-4.

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11

Chakraborty, T. K., and K. K. Gangakhedkar. "Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar." Synthetic Communications 26, no. 11 (June 1996): 2045–56. http://dx.doi.org/10.1080/00397919608003563.

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12

Tao, Junhua, and Robert V. Hoffman. "A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres." Journal of Organic Chemistry 62, no. 18 (September 1997): 6240–44. http://dx.doi.org/10.1021/jo970579s.

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13

Pégorier, Laurent, and Marc Larchevêque. "A general stereocontrolled synthesis of hydroxyethylene dipeptide isosteres." Tetrahedron Letters 36, no. 16 (April 1995): 2753–56. http://dx.doi.org/10.1016/0040-4039(95)00357-i.

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14

Kempf, Dale J. "Dipeptide analogs. Versatile synthesis of the hydroxyethylene isostere." Journal of Organic Chemistry 51, no. 21 (October 1986): 3921–26. http://dx.doi.org/10.1021/jo00371a001.

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15

Wuts, Peter G. M., Allen R. Ritter, and Lynn E. Pruitt. "Synthesis of the hydroxyethylene isostere of Leu-Val." Journal of Organic Chemistry 57, no. 25 (December 1992): 6696–700. http://dx.doi.org/10.1021/jo00051a005.

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16

Jones, D. Michael, Bo Nilsson, and Michael Szelke. "A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres." Journal of Organic Chemistry 58, no. 8 (April 1993): 2286–90. http://dx.doi.org/10.1021/jo00060a052.

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17

BOYD, S. A., R. A. MANTEI, C. N. HSIAO, and W. R. BAKER. "ChemInform Abstract: Stereoselective Syntheses of Hydroxyethylene Dipeptide Isosteres." ChemInform 22, no. 21 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199121267.

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18

Herold, Peter, Rudolph Duthaler, Grety Rihs, and Christof Angst. "A versatile and stereocontrolled synthesis of hydroxyethylene dipeptide isosteres." Journal of Organic Chemistry 54, no. 5 (March 1989): 1178–85. http://dx.doi.org/10.1021/jo00266a034.

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19

Peyrat, Jean-François, Christophe Chaboche, Bruno Figadère, and André Cavé. "A formal stereoselective synthesis of a hydroxyethylene dipeptide isostere." Tetrahedron Letters 36, no. 16 (April 1995): 2757–60. http://dx.doi.org/10.1016/0040-4039(95)00358-j.

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20

Aoyagi, Yutaka, and Robert M. Williams. "General asymmetric synthesis of hydroxymethylene and hydroxyethylene peptide isosteres." Tetrahedron 54, no. 35 (August 1998): 10419–33. http://dx.doi.org/10.1016/s0040-4020(98)00495-5.

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21

DIEDERICH, A. M., and D. M. RYCKMAN. "ChemInform Abstract: Stereoselective Synthesis of a Hydroxyethylene Dipeptide Isostere." ChemInform 25, no. 12 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199412271.

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22

Erdal, Erik P., Pavel Martásek, Linda J. Roman, and Richard B. Silverman. "Hydroxyethylene isosteres of selective neuronal nitric oxide synthase inhibitors." Bioorganic & Medicinal Chemistry 15, no. 18 (September 2007): 6096–108. http://dx.doi.org/10.1016/j.bmc.2007.06.038.

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23

Litera, Jaroslav, Miloš Buděšínský, Ján Urban, and Milan Souček. "Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids." Collection of Czechoslovak Chemical Communications 63, no. 2 (1998): 231–44. http://dx.doi.org/10.1135/cccc19980231.

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Abstract:

By two separate routes were prepared four diastereoisomers of (2R or 2S,5R or 5S)-3-benzyl-5-{(1S)- [(tert-butoxycarbonyl)amino]-2-phenylethyl}tetrahydrofuran-2-ones (11, 12, 17 and 18). Since the furanones were derived from (S)-phenylalanine, absolute configurations of all chiral carbon atoms could be deduced from their 1H NMR spectra. The furanones were easily hydrolyzed to four (2R or 2S,4R or 4S,5S)-2-benzyl-5- [(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylbutanoic acids (20-23), hydroxyethylene isosteres of Phe-Phe peptide bond.

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24

Dragovich, Peter S., Thomas J. Prins, and Ru Zhou. "Formal, Stereoselective Synthesis of Hydroxyethylene Dipeptide Isosteres Utilizing Pseudoephedrine Amides." Journal of Organic Chemistry 62, no. 22 (October 1997): 7872–76. http://dx.doi.org/10.1021/jo9707951.

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25

D'Aniello, Fabiana, Sylvie Géhanne, and Maurizio Taddei. "A convenient approach to hydroxyethylene dipeptide isosteres using allylsilane chemistry." Tetrahedron Letters 33, no. 38 (September 1992): 5621–24. http://dx.doi.org/10.1016/s0040-4039(00)61163-2.

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26

Yang, Xiaoming, Xiaomin Zou, Yiqiu Fu, Ke Mou, Gang Fu, Chao Ma, and Ping Xu. "Synthesis of β‐Secretase Inhibitors Containing a Hydroxyethylene Dipeptide Isostere." Synthetic Communications 37, no. 1 (January 1, 2007): 9–24. http://dx.doi.org/10.1080/00397910600977509.

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27

Nishi, Takahide, Mitsuru Kataoka, and Yasuhiro Morisawa. "Diastereoselective Synthesis of the Hydroxyethylene Dipeptide Isostere of Leu–Val." Chemistry Letters 18, no. 11 (November 1989): 1993–96. http://dx.doi.org/10.1246/cl.1989.1993.

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28

PEGORIER, L., and M. LARCHEVEQUE. "ChemInform Abstract: A General Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres." ChemInform 26, no. 32 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199532205.

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29

CHAKRABORTY, T. K., and K. K. GANGAKHEDKAR. "ChemInform Abstract: Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar." ChemInform 27, no. 36 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199636207.

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30

TAO, J., and R. V. HOFFMAN. "ChemInform Abstract: A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres." ChemInform 29, no. 3 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199803209.

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31

Shin, Hyunik, Kyu Woong Lee, Hyeong-wook Choi, Byung Han Lee, Bo Seung Choi, Jay Hyok Chang, Young Keun Kim, Jae Hoon Lee, Taeho Heo, and Do Hyun Nam. "A Stereodivergent Synthesis of Hydroxyethylene Dipeptide Isostere via Highly Diastereoselective Epoxidation." Synlett, no. 20 (2005): 3136–38. http://dx.doi.org/10.1055/s-2005-921907.

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32

Stuk, Timothy L., Anthony R. Haight, David Scarpetti, Michael S. Allen, Jerome A. Menzia, Timothy A. Robbins, Shyamal I. Parekh, Denton C. Langridge, and Jien-Heh J. Tien. "An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres." Journal of Organic Chemistry 59, no. 15 (July 1994): 4040–41. http://dx.doi.org/10.1021/jo00094a006.

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33

AOYAGI, Y., and R. M. WILLIAMS. "ChemInform Abstract: General Asymmetric Synthesis of Hydroxymethylene and Hydroxyethylene Peptide Isosteres." ChemInform 29, no. 52 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199852094.

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34

PEYRAT, J. F., C. CHABOCHE, B. FIGADERE, and A. CAVE. "ChemInform Abstract: A Formal Stereoselective Synthesis of a Hydroxyethylene Dipeptide Isostere." ChemInform 26, no. 32 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199532206.

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35

Nadin, Alan, Andrew P. Owens, José L. Castro, Timothy Harrison, and Mark S. Shearman. "Synthesis and γ-secretase activity of APP substrate-based hydroxyethylene dipeptide isosteres." Bioorganic & Medicinal Chemistry Letters 13, no. 1 (January 2003): 37–41. http://dx.doi.org/10.1016/s0960-894x(02)00840-5.

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36

Brewer, Matthias, Clint A. James, and Daniel H. Rich. "Synthesis of a Tripeptide Derivative Containing the Gln-Arg Hydroxyethylene Dipeptide Isostere." Organic Letters 6, no. 25 (December 2004): 4779–82. http://dx.doi.org/10.1021/ol047880x.

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37

Sakurai, Mitsuya, Fujio Saito, Yasuo Ohata, Yuichiro Yabe, and Takahide Nishi. "An efficient synthesis of γ-lactones as precursors of hydroxyethylene dipeptide isostere." J. Chem. Soc., Chem. Commun., no. 21 (1992): 1562–63. http://dx.doi.org/10.1039/c39920001562.

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38

Brewer, Matthias, and Daniel H. Rich. "Synthesis of a Tripeptide Derivative Containing the Phe-Arg Hydroxyethylene Dipeptide Isostere." Organic Letters 3, no. 6 (March 2001): 945–48. http://dx.doi.org/10.1021/ol015612i.

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39

Williams, Robert M. "ChemInform Abstract: Asymmetric Syntheses of Unnatural Amino Acids and Hydroxyethylene Peptide Isosteres." ChemInform 31, no. 30 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200030268.

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40

Baker, William R., and John K. Pratt. "Dipeptide isosteres. 2. Synthesis of hydroxyethylene dipeptide isostere diastereomers from a common γ-lactone intermediate. Preparation of renin and HIV-1 protease inhibitor transition state mimics." Tetrahedron 49, no. 39 (January 1993): 8739–56. http://dx.doi.org/10.1016/s0040-4020(01)81896-2.

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41

Sakurai, Mitsuya, Tadashi Hata, and Yuichiro Yabe. "A new synthetic route for the γ-lactone precursors of hydroxyethylene dipeptide isosteres." Tetrahedron Letters 34, no. 37 (September 1993): 5939–42. http://dx.doi.org/10.1016/s0040-4039(00)73819-6.

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42

Radunz, Hans-Eckart, Volker Eiermann, Günther Schneider, and Angelika Riethmüller. "A convenient approach to hydroxyethylene dipeptide isosteres as building blocks for enzyme inhibitors." Tetrahedron 47, no. 10-11 (March 1991): 1887–94. http://dx.doi.org/10.1016/s0040-4020(01)96101-0.

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43

STUK, T. L., A. R. HAIGHT, D. SCARPETTI, M. S. ALLEN, J. A. MENZIA, T. A. ROBBINS, S. I. PAREKH, et al. "ChemInform Abstract: An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres." ChemInform 26, no. 4 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199504237.

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44

Chakraborty, T. K., K. Azhar Hussain, and D. Thippeswamy. "A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucose." Tetrahedron 51, no. 13 (March 1995): 3873–80. http://dx.doi.org/10.1016/0040-4020(95)00109-l.

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45

Wångsell, Fredrik, Karin Gustafsson, Ingemar Kvarnström, Neera Borkakoti, Michael Edlund, Katarina Jansson, Jimmy Lindberg, Anders Hallberg, Åsa Rosenquist, and Bertil Samuelsson. "Synthesis of potent BACE-1 inhibitors incorporating a hydroxyethylene isostere as central core." European Journal of Medicinal Chemistry 45, no. 3 (March 2010): 870–82. http://dx.doi.org/10.1016/j.ejmech.2009.11.013.

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46

KIM, B. H., and H. J. AHN. "ChemInform Abstract: Efficient Synthesis of Hydroxyethylidene and (E)-Alkene Dipeptide Isosteres." ChemInform 28, no. 46 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199746204.

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47

Chakraborty, T. K., and S. Dutta. "Synthesis of a New C2-Symmetric Molecule with Dimeric Hydroxyethylene Isosteric Moiety." Synthetic Communications 27, no. 23 (December 1997): 4163–72. http://dx.doi.org/10.1080/00397919708005464.

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48

Lagu, Bharat R., and Dennis C. Liotta. "Diastereoselective synthesis of the key lactone intermediate for the preparation of hydroxyethylene dipeptide isosteres." Tetrahedron Letters 35, no. 4 (January 1994): 547–50. http://dx.doi.org/10.1016/s0040-4039(00)75834-5.

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49

Thompson, Wayne J., Richard G. Ball, Paul L. Darke, Joan A. Zugay, and J. E. Thies. "Stereoselective synthesis of the hydroxyethylene isostere of the HIV protease (Tyr-Pro) cleavage site." Tetrahedron Letters 33, no. 21 (May 1992): 2957–60. http://dx.doi.org/10.1016/s0040-4039(00)79571-2.

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50

Holladay, Mark W., Francesco G. Salituro, and Daniel H. Rich. "Synthetic and enzyme inhibition studies of pepstatin analogs containing hydroxyethylene and ketomethylene dipeptide isosteres." Journal of Medicinal Chemistry 30, no. 2 (February 1987): 374–83. http://dx.doi.org/10.1021/jm00385a020.

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