Lewisy

Synthetic studies aimed to elucidate the stereostructure of the aggregation pheromone of the male stink bug Erysarcoris lewisi, which is 2-methyl-6-(4 -methylenebicyclo [3 1 0] hexyl)hept-2-en-l-ol was reported. ... 

Allen JR, Harris CR, Danishefsky SJ. Pursuit of optimal carbohydrate-based anticancer vaccines preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBrl, and Lewisy antigens. J Am Chem Soc 2001 123 1890-1897. 

Sagara, N. and Kobayashi, T. (1979). Hebeloma spoliatum appeared from abandoned nest-chambers of Vespula lewisi, a ground wasp. Trans. Mycol. Soc. Japan 20, 266-267 (in Japanese). 

Moran, A.P., Knirel, Y.A., Senchenkova, S.N., Widmalm, G., Hynes, S.O., Jansson, P.-E. Phenotypic variation in molecular mimicry between Helicobacter pylori lipopolysaccharides and human gastric epithelial cell surface glycoforms. Acid-induced phase variation in Lewis 1 and Lewisy expression by H. pylori lipopolysaccharides. J Biol Chem 277 (2002a) 5785-5795. 

Rats, intraperitoneally inoculated with crude holothurin and previously or simultaneously infected by Tripanosoma lewisi had lower parasitemia than in the controls [53]. But, on the contrary, a higher level of parasitemia was observed in rats treated after infection. Sen Lin confirmed these results in mice inoculated with Trypanosoma duttony [54, 55]. 

A simple example of the examination of a proposed structure through synthesis is provided in this section. In 2005, Takita12 proposed the structure of the male-produced aggregation pheromone of the stink bug Eysarcoris lewisi as the sesquisabinene alcohol, ( )-2-methyl-6-(4 -methylenebicyclo[3.1.0]hexyl)hept-2-en-l-ol (8) (Scheme 1). Mori13 synthesized (61 )-8 and (6S)-8 from the enantiomers of citronellal (10). The key steps were the intramolecular addition of an ct-keto carbene to the alkene bond (11—>12) and ( )-selective olefination of 13 to give 14. The 1H- and 13C-NMR spectra of 8 around the trisubstituted double bond at C-2 were different from those of the natural pheromone. 

Scheme 2 Synthesis of the male-produced aggregation pheromone of the stink bug Eysarcoris lewisi. Reagents ...

LMB-9 (B3 (ds scFv)-PE38) a-LewisY-PE38 (ds scFv fusion to PE38 Colorectum, pancreas, esophagus, stomach, breast, NSCLC, GIC, bladder, ovarian NCI/IVAX Phase I 29... 

SGN-15 (BMS-182248/ a-LewisY-doxorubicin Breast,colon, Seattle Genetics/ Three Phase II clinical trials 44,45... 

SGN-25 (BR96-auristatin E) a-LewisY-auristatin E (chimeric) Breast,colon, prostate, lung Seattle Genetics Preclinical development 46... 

Figure 4.11 Elucidation of the correct gross structure of the pheromone of Eysarcoris lewisi by synthesis...

Walter, R. D., Muhlpfordt, H., and Konigk, E. (1970). Comparative studies of the desoxythy-midylate synthesis in Plasmodium chabaudi, Trypanosoma gambiense and Trypanosoma lewisi. Z. Tropenmed. Parasitol. 21,347-357. 

For example, cassette coupling and protecting group manipulations provided trifluoromethansulfonyl (TF) disaccharide 28, which was evolved in solution to the trimeric TF cluster 29 (Scheme 5). Here, epoxide 25 derived from glycal 25 proved to be a powerful donor in reaction with cassette 26 to afford the /3-linked disaccharide 27 (Scheme 5). Similarly, 2,6-STF and STn clusters and the clustered LewisY were also prepared, conjugated to keyhole limpet hemocyanin (KLH) or bovine serum albumin (BSA), and their immunological properties were evaluated as anticancer vaccine. ... 

Darling, T. N., Balber, A. E. and Blum, J. J. (1988) A comparative study of D-lactate and L-lactate formation by four species of Leishmania and of Trypanosoma lewisi and Trypanosoma brucei gambiense. Mol. Biochem. Parasitol. 30 253-258. 

Dixon, H. and Williamson, J. (1970) The lipid composition of blood and culture forms of Trypanosoma lewisi and Trypanosoma rhodesiense compared with that of their environment Comp. Biochem. Physiol. 33 111-128. 

From W. K. Lewisy one of our most valued consultants, we learned early on to go for the fundamentals, to understand what we re doing, to build on a solid foundation—but not to wait until we understand everything before being willing to make a decision. 

Hopp, K.H. Cunningham, L.V. Bromel, M.C. Schermeister, L.J. 8c Kahlil, S.K.W. 1976. In vitro antitrypanosomal activity of certain alkaloids against Trypanosoma lewisi. Lloydia Vol. 39 375-377. 

Kudryashov V, Glunz PW, Williams LJ et al (2001) Toward optimized carbohydrate-based anticancer vaccines epitope clustering, carrier stmcture, and adjuvant all influence antibody response to LewisY conjugates in mice. Proc Natl Acad Sci USA 98 3264-3269... 

Aboko-Cole and Lee (1974) found increased parasitemias in folate deficient rats infected with Trypanosoma lewisi. The deficient animals had increased parasite levels in their blood compared to control animals and remained infected for longer periods of time. The results of studies on immune status in a number of species point to defective cell mediated immune function and a possible reduction in humoral immunity as well. 

Trypanosoma cruzi T. ranarum T. riiodesioise T. mega T. lewisi... 

Preparation of bicyclic alcohol (6/ ,1 S,4 S,5 / )-51, which was converted to the pheromone of Eysarcoris lewisi. 

In vitro anti trypanosomal activity of certain alkaloids against Trypanosoma lewisi , Lloydia, 39, 375-377. 

---