1-amino-2-hydroxycycloalkanecarboxylic acid derivatives

Details 1-amino-2-hydroxycycloalkanecarboxylic acid derivatives 1-amino-2-hydroxycycloalkanecarboxylic acid derivatives

1998-03-10

1999-09-28

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

562505, 562507, C07C 6106, C07C 6104, C07C 6108

Patent

active

059591412

ABSTRACT:
The invention is directed to optically active 1-amino-hydroxycycloalkanecarboxylic acid compounds represented by the formula: ##STR1## wherein n is 0, 1, 2, 3, or 4; methods of their synthesis; and their use as compounds to fix the confirmation of a peptide or protein molecule when introduced into the peptide or protein in the place of a normal amino acid.

REFERENCES:
Database CAPLUS on STN, Acc. No. 1997:564947, Christensen et al., `Does the non-saturable cell entry apply to the charge-free form of amiono acids?,` abstract, 1977.
D.E. Gaitanopoulos et al., Racemic Diastereoisomers of 1-Amino-2-Hydroxycyclopentanecarboxylic Acid J. Med. Chem 19(2):342-344 (1976).
M. Horikawa et al., "Asymmetric Syntheses of Both Enantiomers of .alpha.-Benzylserine and .beta.-Carboxymethylserine" Synlett 253-254 (1997).
Y. Ito et al., "Asymmetric Aldol Reaction of .alpha.-Isocyanocarboxylates with Paraformaldehyde Catalyzed by Chiral Ferrocenylphosphine-Gold (I) Complexes" Tetrahedron Letters 29(2):235-238 (1988).
S.-H. Moon et al., "Efficeint Syntheses of the Four Enantiomers and Diastereomers of .alpha.-Methylthreonine and Both Enantiomers of .alpha.-Methylserine" J. Am. Chem. Soc. 116(16):7405-7406 (1994).
D. Seebach et al., ".alpha.-Alkylation of Threonine" Tetrahedron Letters 24(32):3311-3314 (1983).
Abstract of the presentation at the 72nd Spring Annual Meeting of the Chemistry Society of Japan on Mar. 27, 1997 entitled, "Synthesis and Bioactivity of .alpha., .alpha.-Disubstituted-.beta.-Amino Acid-Introduced Peptides," and an English language translation thereof, along with a set of overhead drawings presented at the meeting.
Abstract of the presentation at the 71st Symposium on Organic Synthesis, Japan on Jun. 5, 1997 entitled, "Synthesis of Compounds for Bioactivity," and an English translation thereof, along with a set of overhead drawings presented at the symposium.

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