4-(N,N-二甲基氨磺酰)-7-异硫氰酸基-2,1,3-苯并恶二唑 | 147611-81-2

• 物质功能分类: 分析化学 - 液相色谱 - HPLC标记试剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 4-(N,N-二甲基氨磺酰)-7-异硫氰酸基-2,1,3-苯并恶二唑
• 中文别名: 4-(N,N-二甲基氨基磺酰)-7-异硫氰基苯并呋咱；4-(N,N-二甲氨基磺酰基)-7-异硫氰基-2,1,3-苯并二唑；4-(N,N-二甲基氨磺酰)-7-异硫氰酸基-2,1,3-苯并恶二唑[用于高效液相色谱标记和埃德曼降解法]
• 英文名称: 7-<(N,N-dimethylamino)sulfonyl>-2,1,3-benzoxadiazol-4-yl isothiocyanate
• 英文别名: DBD-NCS；7-N,N-Dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate；7-isothiocyanato-N,N-dimethyl-2,1,3-benzoxadiazole-4-sulfonamide
• CAS: 147611-81-2
• 化学式: C₉H₈N₄O₃S₂
• 分子量: 284.32
• InChiKey: SUOZAUUDBKHLHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  126°C
• 沸点：
  458.1±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-(N,N-二甲基氨磺酰)-7-异硫氰酸基-2,1,3-苯并恶二唑 在 吡啶 、 三氟乙酸 作用下， 以 吡啶 、 水 、 三氟乙酸 为溶剂， 反应 0.42h， 生成 7-(4-Isobutyl-5-oxo-4,5-dihydro-thiazol-2-ylamino)-benzo[1,2,5]oxadiazole-4-sulfonic acid dimethylamide
  参考文献：
  名称：

  Development of an Efficient Amino Acid Sequencing Method Using Fluorescent Edman Reagent 7-[(N,N-Dimethylamino)sulfonyl]-2,1,3-benzoxadiazol-4-yl Isothiocyanate

  摘要：

  In this paper, a new method is described for N-terminal amino acid sequencing of peptides using the fluorescent reagent 7-[(N,N-dimethylamino)sulfonyl]-2,1,3-benzoxadiazol-4-yl isothiocyanate (DBD-NCS). Sequence determination is carried out by identifying thiazolinone (TZ) amino acids, which are generally unstable and difficult to detect. The employed system can easily and quickly derive TZ amino acids using the Edman reaction with DBD-NCS; these amino acids are also stable enough to be efficiently detected by high-performance liquid chromatography. Resultant detection limits for DBD-TZ amino acids range from 50 fmol to a sub-picomole level (S/N = 3). This system successfully analyzed sequences of Leu(5)-enkephalin (25 pmol) and angiotensin I(100 pmol) using fluorometric detection at 524 nm with excitation at 387 nm.

  DOI：

  10.1021/ac00119a012

文献信息

• [EN] CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1<br/>[FR] SYNTHÈSE CHIMIO-ENZYMATIQUE DE LIRAGLUTIDE, DE SEMAGLUTIDE ET DE GLP-1
  申请人：ENZYPEP B V

  公开号：WO2019170918A1

  公开（公告）日：2019-09-12

  The invention relates to a method for synthesising a peptide comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester comprising a first peptide fragment comprising the sequence His-X- Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nudeophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala -Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z- Gly-Arg-Gly wherein - X is Ala or an α-amino-isobutyric acid (Aib) residue - Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalised with an amino acid or another functional group - Z is Arg or Lys.

  该发明涉及一种合成肽的方法，包括序列His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly，包括酶催化偶联(a) 包含第一肽片段His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(硫)酯的肽C末端酯或硫酯；和(b) 具有N-末端未保护胺基的肽亲核试剂，包括序列H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly，其中- X为Ala或α-氨基异丁酸（Aib）残基，- Y为Lys，该Lys具有自由侧链ε-氨基基团或该Lys的侧链ε-氨基基团被保护基保护或该Lys的侧链ε-氨基基团被氨基酸或其他功能基官能化，- Z为Arg或Lys。
• [EN] CHEMO-ENZYMATIC SYNTHESIS OF SEMAGLUTIDE, LIRAGLUTIDE AND GLP-1<br/>[FR] SYNTHÈSE CHIMIO-ENZYMATIQUE DE SEMAGLUTIDE, DE LIRAGLUTIDE ET DE GLP-1
  申请人：ENZYPEP B V

  公开号：WO2019170895A1

  公开（公告）日：2019-09-12

  The invention relates to a method for preparing a coupling product comprising the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester comprising a first peptide fragment represented by the formula Pq-Wv- His-X-Glu-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein - P represents a protective group at the N-terminal a-amino function of said peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; - W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; - X is Ala or an α-amino-isobutyric acid unit (Aib); - Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalised with an amino acid or another functional group; - Z is Arg or Lys.

  该发明涉及一种制备偶联产物的方法，其包括序列Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly，包括酶催化偶联(a)包括由公式Pq-Wv-His-X-Glu-(硫)酯代表的第一肽段的肽C-末端酯或硫酯；以及(b)包括具有N-末端未保护胺基的肽亲核的第二肽段，其包括序列H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly，其中 - P代表所述肽C-末端酯或硫酯的N-末端α-氨基功能处的保护基，q是具有值为1或0的整数；- W代表一个或多个氨基酸残基，可以相同也可以不同，v是具有值为1或更多的整数，表示氨基酸残基W的数量；- X为Ala或α-氨基异丁酸单元（Aib）；- Y为Lys，该Lys具有自由的侧链ε-氨基基团或使用保护基保护的侧链ε-氨基基团或使用氨基酸或另一功能基团功能化的侧链ε-氨基基团；- Z为Arg或Lys。
• Semi-empirical PM3 calculation reveals the relationship between the fluorescence characteristics of 4,7-disubstituted benzofurazan compounds, the LUMO energy and the dipole moment directed from the 4- to the 7-position
  作者：Seiichi Uchiyama、Tomofumi Santa、Kazuhiro Imai

  DOI：10.1039/a808010k

  日期：——

  with the PM3 calculation is most closely related with the fluorescence characteristics. Using these parameters, the fluorescent 4,7-disubstituted benzofurazan compounds were classified into two groups, and the maximum excitation and emission wavelengths were different between these two groups. These relationships indicated that the fluorescence characteristics of 4,7-disubstituted benzofurazan compounds

  本文通过计算机计算阐明了4,7-二取代苯并呋喃化合物的化学结构与荧光特性（荧光强度，最大激发波长和最大发射波长）之间的关系。我们先前使用4-和7-位取代基的Hammett取代基常数进行的研究表明，苯并呋喃山骨架上的总电子密度和从4-至7-位指向的偶极矩可能会影响荧光特性。这些化合物。选择苯并呋喃骨架上的原子电荷之和，HOMO能量和LUMO能量作为参数，以反映苯并呋喃骨架上的电子密度的总和，并通过AM1和PM3计算得出。还用两个哈密顿量计算了从4位到7位的偶极矩。通过PM3计算获得的LUMO能量和从4位到7位的偶极矩与荧光特性最密切相关。使用这些参数，将荧光的4,7-二取代的苯并呋喃类化合物分为两组，并且最大激发和发射波长在这两组之间是不同的。这些关系表明，4,7-二取代的苯并呋喃类化合物的荧光特性由苯并呋喃类骨架上的总电子密度和从4位到7位的偶极矩确定。此外，我们预测了四个4的荧光特征
• Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1
  申请人：ENZYPEP B.V.

  公开号：US10858414B2

  公开（公告）日：2020-12-08

  The invention relates to a method for preparing a coupling product having the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly. The method includes enzymatically coupling (a) a peptide C-terminal ester or thioester having a first peptide fragment represented by the formula Pq-Wv-His-X-Glu-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine having a second peptide fragment with the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein P represents a protective group at the N-terminal α-amino function of the peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; X is Ala or an α-amino-isobutyric acid unit (Aib); Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalized with an amino acid or another functional group; and Z is Arg or Lys.

  本发明涉及一种制备具有 Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly 序列的偶联产物的方法。该方法包括将 (a) 具有由式 Pq-Wv-His-X-Glu-(thio)ester 代表的第一肽片段的肽 C 端酯或硫酯；和 (b) 具有 N 端未受保护的胺的肽亲核体，其第二肽片段的序列为 H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly 其中 P 代表肽 C 端酯或硫酯的 N 端 α-氨基官能团的保护基团，q 是数值为 1 或 0 的整数； W 代表一个或多个氨基酸残基，它们可以相同或不同，v 是一个数值为 1 或以上的整数，代表氨基酸残基 W 的数目； X 是 Ala 或 α-氨基异丁酸单元（Aib）； Y 是 Lys，其中 Lys 具有一个游离侧链 ε-氨基基团，或一个用保护基团保护的侧链 ε-氨基基团，或一个用氨基酸或其他官能团官能化的侧链 ε-氨基基团；和 Z 是 Arg 或 Lys。
• Chemo-enzymatic synthesis of Semaglutide, Liraglutide and GLP-1
  申请人：ENZYPEP B.V.

  公开号：US10883132B2

  公开（公告）日：2021-01-05

  A method for synthesizing a peptide having the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly is disclosed. The method includes enzymatically coupling: (a) a peptide C-terminal ester or thioester having a first peptide fragment with the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine having a second peptide fragment with the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly; wherein: X is Ala or an α-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalized with an amino acid or another functional group; and Z is Arg or Lys.

  本发明公开了一种合成具有 His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly 序列的多肽的方法。该方法包括酶偶联： (a) 具有序列为 His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester 的第一肽片段的肽 C 端酯或硫酯；和 (b) 具有 N-末端未受保护胺的肽亲核剂，其第二肽片段的序列为 H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly； 其中： X 是 Ala 或 α-氨基异丁酸（Aib）残基； Y 是赖氨酸，赖氨酸具有游离的侧链ε-氨基，或者赖氨酸的侧链ε-氨基被保护基保护，或者赖氨酸的侧链ε-氨基被氨基酸或其它官能团官能化；以及 Z 是 Arg 或 Lys。