MALDI-MS determination of cyclic peptidomimetic sequences on single beads directed toward the generation of libraries

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 1-4

  Yu, Zhiguang ^a   Yu, X Christopher ^b   Chu, Yen Ho ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b Camp Chem Instrum Ctr Ohio S   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM;

AMINO ACID SEQUENCE; ARTICLE; BORRELIA BURGDORFERI; CYCLIZATION; DRUG RECEPTOR BINDING; LIGAND BINDING; NONHUMAN; OLIGOMERIZATION; PEPTIDE SYNTHESIS; PROTEIN DEGRADATION; REACTION ANALYSIS;

BORRELIA; BORRELIA BURGDORFERI;

EID: 0031983804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10485-3     Document Type: Article

References (21)

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11. Wiesmuller, K.-H.; Feiertag, S.; Fleckenstein, B.; Kienle, S.; Stoll, D.; Herrmann, M.; Jung, G. In Combinatorial Peptide and Non-Peptide Libraries; Jung, G., Ed.; VCH: Weinheim (Germany), 1996; pp. 203-246; Spatola, A.F.; Romanovskis, P. In Combinatorial Peptide and Non-Peptide Libraries; Jung, G., Ed.; VCH: Weinheim (Germany), 1996; pp. 327-347; Kates, S.A.; Sole, N.A.; Albericio, F.; Barany, G. In Peptides: Design, Synthesis, and Biological Activity; Basava, C.; Anantharamaiah, G.M., Eds.; Birkhauser: Boston, 1994; pp. 39-58; Tumelty, D.; Vetter, D.; Antonenko, V.V. J. Chem. Soc., Chem. Commun. 1994, 1067-1068.
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15. The methionine residue was engineered to mediate cleavage of peptides from the resin and the lysine (or arginine) was included to introduce a common protonation site for ease of MS detection and, if necessary, post-cleavage modification (e.g., fluorescent tag labeling). Two β-Ala residues were used as a spacer.
16. Side chains of peptides were deprotected using a cleavage cocktail of 82.0% TFA, 4.0% water, 4.0% thioanisole, 6.0% mercaptoacetic acid, and 4.0% phenol at rt for 4 hours, and the resin was washed with ethyl ether to remove scavengers.
17. -1. All separations were monitored at 214 nm.
18. The MALDI-MS analysis was conducted using a Kratos Kompact MALDI-III instrument. Saturated solution of α-cyano-4-hydroxy-cinnamic acid in 50:50 water/acetonitrile was used as the matrix. Sample (1.0 μL) was mixed with the matrix solution (1.0 μL) on a slide for MS analysis. The instrument was calibrated externally with substance P and leucine-enkephalin.
19. 2-AVQQEGAE(OH)BBKM peptide was not cyclized on the TentaGel support.
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21. 4-X). X represents dimethylamine for the +27 Da adduct, and morpholine for the +69 Da adduct.