By Miklos Bodanszky
Through the years 1980-81, as visitors of the Deutsches Wollforschungsinstitut in Aachen, Germany, we have been engaged on a small publication entitled, "Principles of Peptide Synthesis". within the library of the Institute we famous that the volumes of Houben-Weyl's Handbuch der Organischen Chemie facing peptide synthesis have been lots in use that they have been able to crumble as the researchers of the Institute consulted them with awesome regularity. They have been trying to find references, yet much more for experimental info that can be tailored to the actual challenge they occurred to stand. In making plans a brand new artificial activity they attempted to lean at the adventure of others in analogous events. This advised to us smaller and for that reason extra tractable booklet will be wanted, a quantity which might be saved on or close to the bench to make examples of basic tools on hand within the laboratory. the sort of assortment may shop quite a few brief journeys to the library, some extent quite vital the place a library good built with the resources of the literature of peptide synthesis isn't close to handy. additionally, we inspiration that the envisaged ebook might be welcome through people who find themselves extra versed in English than in German. To the simplest of our wisdom no related ebook is on the market.
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Blocking of the a-Carboxyl Group 3. Melting points and specific rotations of the N-hydroxymethylphthalimide esters of several benzyloxycarbonylamino acids are reported in ref. I. 4. The phthalimidomethyl esters ofbenzyloxycarbonylamino acids were hydrogenated in methanol containing an equimolecular amount of p-toluenesulfonic acid. After the removal of the catalyst and the solvent the p-toluenesulfonate salts of amino acid N-hydroxymethylphthalimide esters were crystallized from ethanolether. 5.
5. butyl dicarbonate. It melts at 20-22 DC and should be stored in a refrigerator. 6. g. 0 ml, 10 mmol) to a solution of the BOC-amino acid in absolute ethanol and diluting the solution with ether. A. Introduction of Amine Protecting Groups 6. The Biphenylylisopropyloxycarbonyl (Bpoc) Group (1, 2] a. 9 g, 120 mmol) in dichloromethane (50 ml) is added, dropwise, in about 1/2 hour. Stirring is continued at o °e overnight. During this time most of the heavy precipitate which formed during the addition of the chlorocarbonate dissolves.
Spectrum shows two carbonyl bands, at 1717 and 1765 cm -1. 4 g, 100 mmol) in dichloromethane (100 ml) is added dropwise. Stirring is continued at about 4 °C for 5 hours. Ice water (about 200 ml) is added, the organic layer washed with N HCI and then several times with water. It is dried over anhydrous Na2 S04 and evaporated in vacuo to dryness. The crystalline residue, 2-(4-biphenylyl)-2-propyl 4-methoxycarbonylphenyl carbonate  is recrystallized from ethyl acetate-ether and from dichloromethane22 A.
The Practice of Peptide Synthesis by Miklos Bodanszky