The Molecular and Crystal Structure of tert-Butyl N^α-tert-Butoxycarbonyl-_L-(S-trityl)cysteinate and the Conformation-Stabilizing Function of Weak Intermolecular Bonding

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概要

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• The title compound, C_<31>H_<37>NO_4S{systematic name : (R)-tert-butyl-2-[(tert-butoxycarbonyl)]-3-(tritylsulfanyl)propanoate}is an _L-cysteine derivative with three functions : NH_2, COOH and SH, blocked by protecting groups tert-butoxycarbonyl, tert-butyl and trityl, respectively. The main chain of the molecule adopts the extended, nearly all-trans C_5 conformation with the intramolecular N-H…O=C hydrogen bond. The urethane group is not involved in any intermolecular hydrogen bonding. Only weak intermolecular hydrogen bonds and hydrophobic contacts are observed in the crystal structure. These are C-H…O hydrogen bonds and CH/π interactions with donor…acceptor distances, C…O ca.3.5A and C…C ca.3.7A, respectively. The first type of interaction links phenyl H-atoms and carbonyl groups. The second type of interaction is formed between a methyl group of the tert-butyl fragment and a trityl phenyl ring. The resulting molecular conformation in the crystal is very close to an ab initio minimum energy conformer of the isolated molecule. The extended C_5 conformation of the main peptide chain is the same and there is slight discrepancy in the disposition of trityl phenyl rings. Their small dislocation creates the possibility of forming the entire network above of extensive, specific, weak intermolecular interactions ; these constrain the molecule and permit it to retain the minimum energy C_5 conformation of its main chain in the solid state. In contrast, in n-hexane solution, where such specific interactions cannot occur, only a small population of the molecules adopts the extended C_5 conformation.

• 公益社団法人日本薬学会の論文
• 2001-04-01

著者

• Rzeszotarska B

  Institute Of Chemistry University Of Opole

• KOZIOL Anna

  Faculty of Chemistry, Maria Curie-Sklodowska University

• MASIUKIEWICZ Elzbieta

  Department of Organic Chemistry, University of Opole

• RZESZOTARSKA Barbara

  Department of Organic Chemistry, University of Opole

• SZADY Beata

  Faculty of Chemistry, Maria Curie-Sklodowska University

• BRODA Malgorzata

  Department of Organic Chemistry, University of Opole

• Szady Beata

  Faculty Of Chemistry Maria Curie-sklodowska University

• Rzeszotarska Barbara

  Department Of Organic Chemistry University Of Opole

• Broda Malgorzata

  Institute Of Chemisty University Of Opole

• Masiukiewicz E

  Institute Of Chemisty University Of Opole

• Masiukiewicz Elzbieta

  Department Of Organic Chemistry University Of Opole

• Koziol Anna

  Faculty Of Chemistry Maria Curie-sklodowska University

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