16310-13-7Relevant articles and documents
Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline (1,3-thiazolidine-2-carboxylic acid)
Engel, Wolfgang,Schieberle, Peter
, p. 5394 - 5399 (2002)
Fructose was reacted in the presence of either cysteamine (model A) or isothiaproline (model B) in aqueous buffer at 145 °C and pH 7.0. Application of an aroma extract dilution analysis on the bulk of the volatile compounds formed in model A revealed 5-acetyl-3,4-dihydro-2H-1,4-thiazine (19), N-(2- mercaptoethyl)-1,3-thiazolidine (16), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (15), and 2-acetyl-2- thiazoline (11) as the key aroma compounds among the 10 odorants detected. A similar set of aroma compounds was formed when isothiaproline was reacted (model B), but the flavor dilution factors were generally lower. Substitution of the buffer by silica gel/water (9 + 1 w/w) in both models and application of 150 °C for 10 min also gave the same key odorants from both thio compounds; however, under these conditions isothiaproline was the better precursor of, in particular, 19 and 11. Quantitative measurements performed by means of stable isotope dilution assays revealed a significant effect of the pH on odorant formation. For example, in model A, formation of 19 as well as of 11 was suppressed at pH values 5.0. A clear maximum was, however, found for 19 at pH 7.0 (~1 mol % yield), whereas 11 increased with increasing pH from 7.0 to 9.0.
Preparation of optically active 2-thiazolidinecarboxylic acid by asymmetric transformation
Shiraiwa, Tadashi,Katayama, Takashi,Ishikawa, Joji,Asai, Takeshi,Kurokawa, Hidemoto
, p. 1180 - 1183 (1999)
Cysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R,3R)- or (2S,3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2- thiazolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC. The (-)- and (+)- 2-THC obtained were determined to be enantiopure forms by comparing their powder X-ray diffraction patterns with that of (RS)-2-THC. The absolute configurations of (-)- and (+)-2-THC were estimated based on molar rotations of (2R,4R)- and (2S,4R)-2,4- thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and (-)- and (+)-2-THC. ()-2THC was determined to have the (R)-configuration, and (+)- 2-THC to have the (S)-configuration.
Palladium-unleashed proteins: Gentle aldehyde decaging for site-selective protein modification
Brabham, Robin L.,Spears, Richard J.,Walton, Julia,Tyagi, Swati,Lemke, Edward A.,Fascione, Martin A.
supporting information, p. 1501 - 1504 (2018/02/19)
Protein bioconjugation frequently makes use of aldehydes as reactive handles, with methods for their installation being highly valued. Here a new, powerful strategy to unmask a reactive protein aldehyde is presented. A genetically encoded caged glyoxyl aldehyde, situated in solvent-accessible locations, can be rapidly decaged through treatment with just one equivalent of allylpalladium(ii) chloride dimer at physiological pH. The protein aldehyde can undergo subsequent oxime ligation for site-selective protein modification. Quick yet mild conditions, orthogonality and powerful exposed reactivity make this strategy of great potential in protein modification.
Anti-heparin peptides
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, (2008/06/13)
The invention concerns a compound exhibiting an anti-heparin activity, of formula Z Bm ! (AXA)x Bn ! (AXA)y Bo (AXA)z Bp, the diagnostic reagents comprising it and the use of said compound in an in vitro diagnostic test of a medicine for anti-heparin activity.