N-(2-Carboxyethyl)-2,5-dideoxy-2,5imino-D-mannonic acid [(3R, 4R, 5R)1-( 2-carboxyethyl)-3,4-dihydroxy5- hydroxymethyl-L-proline]

被引:1
|
作者
Edgeley, David S. [1 ]
Fernando Martinez, R. [2 ]
Jenkinson, Sarah F. [2 ]
Nash, Robert J. [3 ]
Fleet, George W. J. [2 ]
Thompson, Amber L. [1 ]
机构
[1] Univ Oxford, Dept Chem Crystallog, Chem Res Lab, Oxford OX1 3TA, England
[2] Univ Oxford, Dept Organ Chem, Chem Res Lab, Oxford OX1 3TA, England
[3] Phytoquest Ltd, IBERS, Aberystwyth SY23 3EB, Ceredigion, Wales
来源
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2012年 / 68卷
关键词
D O I
10.1107/S1600536812037488
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
The absolute stereochemistry of the title compound, C9H15NO7, was determined from the use of d-glucuronolactone as the starting material. The compound crystallizes as the zwitterion. The five-membered ring adopts an envelope conformation with the-CH2OH-substituted C atom forming the flap. An intramolecular N-H center dot center dot center dot O hydrogen-bond occurs. In the crystal, the compound exists as a three-dimensional OH center dot center dot center dot O intermolecular hydrogen-bonded network with each molecule acting as a donor and acceptor for four hydrogen bonds.
引用
收藏
页码:O2865 / +
页数:8
相关论文
共 50 条
  • [21] SYNTHESIS OF HOMOCHIRAL BETA-HYDROXY-ALPHA-AMINO-ACIDS [(2S,3R,4R)-3,4-DIHYDROXYPROLINE AND (2S,3R,4R)-3,4-DIHYDROXYPIPECOLIC ACID] AND OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL [DAB1] AND FAGOMINE [1,5-IMINO-1,2,5-TRIDEOXY-D-ARABINO-HEXITOL]
    FLEET, GWJ
    WITTY, DR
    TETRAHEDRON-ASYMMETRY, 1990, 1 (02) : 119 - 136
  • [22] SIMPLE SYNTHESIS OF (-)-DEOXYMANNOJIRIMYCIN AND (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID VIA REGIOSELECTIVE HYDROLYSIS
    PARK, KH
    YOON, YJ
    LEE, SG
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18): : 2621 - 2623
  • [23] Photochromic properties of five complexes derived from 1, 3, 5-benzenetricarboxylic acid and 1-(2-carboxyethyl)-4,4′-bipyridinium bromide
    Yang, Fengyi
    Chen, Jiali
    Liu, Jinjian
    POLYHEDRON, 2023, 241
  • [24] (3R,4R)-2,2,5,5-Tetraphenyltetrahydrofuran-3,4-diol Assisted, L-proline-Catalyzed Michael Addition of Acetone to Nitroalkenes
    Hu, Xiaoyun
    Shan, Zixing
    Qing, Chang
    LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (07) : 493 - 496
  • [25] Novel potassium N-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxylhex-1-yl]-L-amino acid dichloroplatinates(II) with high anti-tumor activity and low side reaction
    Wang, Yuji
    Kang, Guifeng
    Liu, Jiawang
    Zhao, Ming
    Wu, Jianhui
    Zhang, Xiaoyi
    Li, Ye
    Zhong, Xiaobo
    Yang, Yifan
    Peng, Shiqi
    METALLOMICS, 2012, 4 (05) : 441 - 447
  • [26] Crystal structure of (3R,4R,5R)-5-iodomethyl-3,4-O-isopropylidenedioxy-phenylamino-pyrrolidine-2-one, C14H17IN2O3
    Henkel, S
    Shaw, D
    Jäger, V
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2001, 216 (04): : 611 - 612
  • [27] STRUCTURE OF (+)-(3S,4R,5R,1'R,2'S,5'R)-TETRACARBONYL((3,4-ETA-2)-5-[5'-METHYL-2'-(1-METHYLETHYL)CYCLOHEXYLOXY]-2(5H)-FURANONE)IRON
    ENDERS, D
    SCHMITZ, T
    RAABE, G
    KRUGER, C
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 37 - 40
  • [28] 5-{(2S,3R,4S,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydropyran-2-yloxy]tetrahydropyran-2-yloxy}-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one monohydrate
    Chen, Yuzhen
    Wang, Airong
    Gao, Haiyan
    Niu, Shengyang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1901 - U3554
  • [29] (+)-(1S,2S,3S,4R,5R)-N-(1,3-Dihydroxyprop-2-yl)-2,3,4-trihydroxy-5-(hydroxymethyl)-1-cyclohexanaminium picrate
    Zhu, JR
    Chang, HJ
    Feng, XL
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1498 - O1500
  • [30] SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE
    FLEET, GWJ
    FELLOWS, LE
    SMITH, PW
    TETRAHEDRON, 1987, 43 (05) : 979 - 990