Anthranicine, an Unusual Cyclic Hexapeptide from Acremonium sp. A29-2004

Anthranicine, a cyclic hexapeptide containing anthranilic acid and pipecolic acid, was isolated from a mycophilic Acremonium species. The structure and stereochemistry of the compound featuring two D-configurated amino acids are discussed.

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Synthesis of the cyclic hexapeptide echinocandin D. New approaches to the asymmetric synthesis of .beta.-hydroxy .alpha.-amino acids

Journal of the American Chemical Society ◽

10.1021/ja00257a041 ◽

1987 ◽

Vol 109 (23) ◽

pp. 7151-7157 ◽

Cited By ~ 169

Author(s):

David A. Evans ◽

Ann E. Weber

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

New Approaches ◽

Cyclic Hexapeptide

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ChemInform Abstract: Decarbonylation of α-Tertiary Amino Acids Application to the Synthesis of Polyhydroxylated Indolizidines from D,L-Pipecolic Acid.

ChemInform ◽

10.1002/chin.199902052 ◽

2010 ◽

Vol 30 (2) ◽

pp. no-no

Author(s):

M. J. MARTIN-LOPEZ ◽

R. RODRIGUEZ ◽

F. BERMEJO

Keyword(s):

Amino Acids ◽

Pipecolic Acid ◽

Tertiary Amino

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Amino group requirement for in vitro intestinal transport of amino acids

American Journal of Physiology-Legacy Content ◽

10.1152/ajplegacy.1962.202.1.171 ◽

1962 ◽

Vol 202 (1) ◽

pp. 171-173 ◽

Cited By ~ 10

Author(s):

Richard P. Spencer ◽

Ted M. Bow ◽

Mary Anne Markulis

Keyword(s):

Amino Acids ◽

Acetic Acid ◽

Cinnamic Acid ◽

Concentration Gradient ◽

Anthranilic Acid ◽

Intestinal Transport ◽

Amino Group ◽

Phenylpyruvic Acid ◽

Phenyllactic Acid

The amino group requirement for transintestinal transport of amino acids against a concentration gradient was investigated using hamster everted intestinal sacs. Although glycine (5 x 10–3 m) was transported against a concentration gradient, acetic acid was not. Similarly, l-phenylalanine was transported, whereas phenylpyruvic acid, phenylpropionic acid, phenyllactic acid, and cinnamic acid were not. l-Tryptophan was transported, but indolyllactic acid was not. The amino group was thus essential for transport by this system. n-Methylglycine and l-proline were accumulated from mucosa to serosa against a concentration gradient. Hence, one hydrogen of the amino group can be replaced. However, n-phenylglycine was not accumulated across these preparations, suggesting that the moiety replacing the amino hydrogen can not be sterically bulky. α-l-Alanine was transported against a concentration gradient from mucosa to serosa, but ß-alanine was not. This is in contrast to other systems which accumulate ß-alanine against a concentration gradient. Anthranilic acid, with the amino group in a relative ß position, was also not accumulated across everted intestinal sacs.

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