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Tetrahedron Letters

Volumn 33, Issue 15, 1992, Pages 2067-2068

Beckmann rearrangement of N-(α-hydroxyiminoalkylphosphonyl)amino acids. A convenient synthetic approach to novel peptide-transition-state analogs.

(3) Breuer, Eli a Zaher, Hisham a Tashma, Zeev a

a HEBREW UNIVERSITY OF JERUSALEM (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0026545423 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(92)88143-S Document Type: Article

Times cited : (12)

References (20)

1
- 0016904563
- (1976) Ann. Rev. Biophys. Bioeng. , vol.5 , pp. 271
- Wolfenden¹

2
- 0004164847
- M.I. Page, A. Williams, Royal Society of Chemistry, London
- (1987) Enzyme Mechanisms , pp. 97
- Wolfenden¹ Frick²

3
- 0023984844
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 2282
- Tramontano¹ Amman² Lerner³

4
- 0000358942
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2174
- Jacobs¹ Schultz² Sugasawara³ Powell⁴

5
- 0025950280
- (1991) Biochemistry , vol.30 , pp. 8165
- Kaplan¹ Bartlett²

6
- 37049073703
- Stereoselectivity in fragmentation and rearrangement of ?-hydroxyimino-phosphinates and -phosphonates. A synthetic approach to acylphosphon- and phosphor-amidates. Crystal structures of methyl (E)-?-hydroxyimino-benzylphenylphosphinate and methyl benzoylphenylphosphonamidate
- (1990) Journal of the Chemical Society, Perkin Transactions 1 , pp. 3263
- Breuer¹ Schlossman² Safadi³ Gibson⁴ Chorev⁵ Leader⁶

7
- 84918697287
- E. Breuer, H. Zaher, Z. Tashma, in preparation.

8
- 0025641566
- (1990) J. Org. Chem. , vol.55 , pp. 6147
- Breuer¹ Safadi² Chorev³ Gibson⁴

9
- 0026031690
- (1991) Tetrahedron , vol.47 , pp. 1257
- Breuer¹ Safadi² Chorev³ Vincze⁴ Bel⁵

10
- 84918676898
- in press.
- (1992) Pharm. Res.
- Golomb¹ Schlossman² Saadeh³ Van Gelder⁴ Levi⁵ Breuer⁶

11
- 84918698386
- 9 a naturally occurring inhibitor of aspartic proteinases, is also considered a TS analog of a shortened dipeptide, lacking the nitrogen of the C-terminal acid.

12
- 0017102145
- (1976) Fed. Proc., Fed. Am. Soc. Exp. Biol. , vol.35 , pp. 2494
- Marshall¹

13
- 0017091634
- (1976) J. Biol. Chem. , vol.251 , pp. 7088
- Maciniszyn¹ Hartsuck² Tang³

14
- 0000586297
- (1991) J. Org. Chem. , vol.56 , pp. 4791
- Breuer¹ Mahajna² Quin³ Quin⁴

15
- 84918681982
- 31P NMR: δ = 7.9 ppm (septet, J = 11 Hz).

16
- 84918689285
- 1H: 7.76 (2H, m), 7.42 (1H, m), 7.36 (2H, m) 3.6 (3H, d, J = 12 Hz), 4.04 (2H, q), 3.95 (2H, m), 1.15 (3H, t).

17
- 84918666640
- 31P: δ (ppm) = 7.25 and 6.84 (two sextets, J = 11 Hz each).

18
- 84918706466
- 1H: (E-2b): 7.46 (2H), 7.26 (3H) 4.05 (2H) 3.54–3.6 (6H) 1.24 (3H).

19
- 84918696981
- −1.

20
- 84918707344
- −1.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.