ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Because of its overall steric resemblance to the phenylalanine analogue, carboranylalanine, the title compound was prepared by the modified Strecker synthesis of Patel & Worsley. The use of (S)-(-)-α-methylbenzylamine in the synthesis, the positive trend of [α]D with increasing protonation, and the thin-layer chromatographic behaviour of synthetic diastereomeric dipeptides are strong indications that the configuration at the asymmetric carbon atom is S (natural L). Its optical purity was ascertained by purification via the quinine and ephedrine salts of t-butoxy-carbonyl-adamantylalanine. The new amino acid shall be used for studies of structure-activity relationships of phenylalanine and leucine residues in biologically active peptides. In addition, a convenient synthesis in excellent yield of the starting material, 2-(1-adamantyl)-ethanal, by Pfitzner-Moffat oxidation of 2-(1-adamantyl)-ethanol is described.
Additional Material:
7 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620405
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