Synthesis of an α-dehydro β-amino acid derived cyclic peptide as a constrained β-turn mimic

Arkivoc

Volumn 2001, Issue 8, 2001, Pages 20-26

  Rajesh, S ^a   Srivastava, Jyoti ^a   Bannerji, Biswadip ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; COBALT CHLORIDE; CYCLOPEPTIDE; EPOXIDE;

ARTICLE; CATALYSIS; CYCLIZATION; HYDROGEN BOND; RING CLOSING METATHESIS; SYNTHESIS;

EID: 3242671790     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

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21. For peptides derived from dehydro amino acids see: a) Stammer, C.H. Chemistry and Biochemistry of Amino Acids, Peptides and Protein (Ed. Weinstien, B.), 1982, Vol IV, p3, Marcel Dekker, New York.
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26. The relative stereochemistry of epoxides 1a and 1b was assigned based on the following protocol. The similarity in the sign and magnitude of optical rotation for 1b, prepared by Sharpless's as well as by polyaniline supported cobalt catalysed procedure, helped us to assign the indicated absolute stereochemistry. (Diagram presented)
27. 6 thereby indicating the presence of intramolecular hydrogen bond. A similar protocol was followed for ascertaining the intramolecular hydrogen bond in 3c and 4a.
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31. 3 3a: δ 7.53 (m, 1H), 7.46(s, 1H), 7.12-7.34 (m, 8H), 6.94 (m, 1H), 6.83 (m, 2H), 6.60 (m, 2H), 5.07 (m, 1H), 4.70 (bs, 1H), 4.42 (m, 1H), 4.35 (bs, 1H), 4.04 (d, J = 12.6Hz, 1H), 3.98 (d, J = 12.6Hz, 1H), 3.87 (m, 1H), 3.73 (s, 3H), 3.69 (s, 3H), 3.63 (s, 3H), 3.37 (m, 1H), 2.21 (m, 1H), 2.07 (m, 1H), 1.95 (s, 3H). Mass (m/z): 631(M+1, 20%), 386 (100%), 297 (20%), 212 (50%), 175 (15%), 126 (20%), 91 (20%).
32. -1) 3404.2 (broad), 2957.5, 1741.6, 1679.5, 1509.3, 1244. Mass (m/z): 641 (M+1, 80%), 412 (100%), 323 (10%), 212 (30%).
33. +, 100%), 557 (35%), 317 (25%), 214 (37%).