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Synthesis of the serine equivalent, (2R) and (2S)-amino-3-butenol derivatives. Synthetic approaches to the metal chelating poly-amino acid, “aspergillomarasmine A”

✍ Scribed by Yasufumi Ohfune; Natsuko Kurokawa

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
248 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Chiral synthons, equivalent to the C3 amino acid serine, were synthesized in both (2&) and (2s) form from 9 or L_-methionine respectively; Utilizationof this synthon inthe construction of metal chelating poly-amino acid aspergillomarasmineA skeleton is presented.

Poly-amino acids, in which amino acid moieties are connected by an N-alkyl bond, have received considerable attention owing to their biological and metal chelating activities.

1 Synthetic studies of mugineic acids(i.e., 2'-deoxymugineic acid(l)) constructed from three C4 amino acid units have been reported by us 2 and Nozoe 3 independently, using the reductive amination method with sodium cyanoborohydride(NaBH3CN). 4 However, poly-amino acids containing a C3 amino acid

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