Asymmetric syntheses of 5- and 6-membered carbocyclic serine analogs via an intramolecular Strecker synthesis

Chirality

Volumn 9, Issue 5-6, 1997, Pages 459-462

  Ohfune, Yasufumi ^a   Nanba, Kousuke ^a   Takada, Ichinori ^a   Ran, Toshiyuki ^b   Horikawa, Manabu ^b   Nakajima, Terumi ^b  

^a Osaka Prefecture University   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

substituted serine; 1 amino 2 hydroxycyclohexanecarboxylic acid; 1 amino 2 hydroxycyclopentanecarboxylic acid; Chiral transfer; Conformationally restricted amino acid; Imine enamine equilibrium

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; CYCLOSERINE; KETONE; NITRILE; PHENYLALANINE DERIVATIVE; SERINE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; PROTEIN CONFORMATION; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030987503     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<459::AID-CHIR11>3.0.CO;2-N     Document Type: Article

References (11)

1. (a) Walsh, C. Enzyme reaction mechanisms. San Francisco; Freeman, 1979: 94-97.
2. (b) Cleland, W.W., Kreevoy, M.M. Low-barrier hydrogen bonds and enzymic catalysis. Science 264: 1887-1890, 1994, and references cited therein.
3. For a recent example, see: Mickos, H., Sundberg, K, Liming, B. Synthesis, NMR spectra and function of peptides with α-methylserine attached to the RGD sequence of osteopontin. Acta Chem. Scand. 46: 989-993, 1992.
4. Moon, S.-H., Ohfune, Y. Efficient syntheses of the four enantiomers and diastereomers of α-methylthreonine and both enantiomers of α-methylserine. J. Am. Chem. Soc. 116: 7405-7406, 1994, and references cited therein.
5. The synthesis of the 5-membered ring analog 1 has been reported in racemic form. See: Gaitanopoulous, D.E., Nash, J., Dunn, D.L, Skinner, C.G. Racemic diastereomers of 1-amino-2-hydroxycyclopentanecarboxylic acid. J. Med. Chem. 19:342-344, 1976.
6. Moriarty, R.M., Hou, K.-C. α-Hydroxylation of ketones using o-iodosolbenzoic acid. Tetrahedron Lett. 25:691-694, 1984.
7. Kunz, H., Sager, W., Pfrengle, W., Schanzenbach, D. Reversal of asymmetric induction in stereoselective Strecker synthesis of galactosyl amine as the chiral matrix. Tetrahedron Lett. 29: 4397-4400, 1988.
8. 2O) δ 1.48-2.23 (m, 6 H), 4.37 (dd, 1 H, J = 7.5, 7.5 Hz).
9. 1. Z: 2. Density: 1.255. MU: 6.830. R-factors: R = 0.049, Rw = 0.042. Goodness of fitt = 3.010.
10. 2O) δ 1.36 (dddd, 1 H, J = 3.4, 3.4, 13.2, 13.2 Hz), 1.50-1.65 (m, 2 H), 1.75-1.90 (m, 3 H), 2.10 (ddd, l H, J = 3.4, 3.4, 13.2 Hz), 2.35 (ddd, 1 HJ = 2.5, 2.5, 13.2 Hz), 3.80 (dd, 1 H, J = 4.4, 11.7 Hz).
11. 1. Z: 2. Density: 1.224. MU: 6.566. R-factors: R = 0.019, Rw - 0.054. Goodness of fitt = 5.820.