Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis

被引:18
作者
Adamczyk, M [1 ]
Akireddy, SR [1 ]
Reddy, RE [1 ]
机构
[1] Abbott Labs, Div Diagnost, Div Organ Chem Res, Abbott Pk, IL 60064 USA
关键词
D O I
10.1016/S0957-4166(99)00329-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A versatile chiral synthesis of the bone collagen cross-link, (+)-deoxypyridinoline (Dpd, 1) was described starting from a 3-hydroxypyridine derivative (2) via sequential introduction of three amino acid chains followed by hydrolysis. The key synthon 2, was prepared from vitamin B-6 (6). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3107 / 3110
页数:4
相关论文
共 36 条
  • [1] Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues
    Adamczyk, M
    Johnson, DD
    Reddy, RE
    [J]. TETRAHEDRON, 1999, 55 (01) : 63 - 88
  • [2] Collagen cross-links:: a convenient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate
    Adamczyk, M
    Johnson, DD
    Reddy, RE
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (04) : 775 - 781
  • [3] Total synthesis of deoxypyridinoline, a biochemical marker of collagen turnover
    Allevi, P
    Longo, A
    Anastasia, M
    [J]. CHEMICAL COMMUNICATIONS, 1999, (06) : 559 - 560
  • [4] Relationship between biochemical markers of bone turnover and bone scintigraphic indices in assessment of Paget's disease activity
    Alvarez, L
    Peris, P
    Pons, F
    Guanabens, N
    Herranz, R
    Monegal, A
    Bedini, JL
    Deulofeu, R
    deOsaba, MJM
    MunozGomez, J
    Ballesta, AM
    [J]. ARTHRITIS AND RHEUMATISM, 1997, 40 (03): : 461 - 468
  • [5] A RAPID PROCEDURE FOR PURIFYING LARGE AMOUNTS OF PYRIDINOLINE CROSS-LINKS OF BONE
    ARBAULT, P
    GINEYTS, E
    GRIMAUX, M
    SEGUIN, P
    DELMAS, PD
    [J]. JOURNAL OF LIQUID CHROMATOGRAPHY, 1994, 17 (09): : 1981 - 1993
  • [6] BILEZIKAN JP, 1996, PRINCIPLES BONE BIOL
  • [7] Blake Glen M., 1996, P1313
  • [8] URINARY PYRIDINIUM CROSS-LINKS AS MARKERS OF BONE-RESORPTION IN TUMOR-ASSOCIATED HYPERCALCEMIA
    BODY, JJ
    DELMAS, PD
    [J]. JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 1992, 74 (03) : 471 - 475
  • [9] Validation of a high-performance liquid chromatographic assay for lysylpyridinoline in urine: A potential biomarker of bone resorption
    Casserly, UM
    ORorke, A
    Power, MJ
    Fottrell, PF
    [J]. ANALYTICAL BIOCHEMISTRY, 1996, 242 (02) : 255 - 260
  • [10] AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES
    CONNELL, RD
    REIN, T
    AKERMARK, B
    HELQUIST, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3845 - 3849