N-t-butyloxycarbonyl-D-alanylglicine | 66444-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-t-butyloxycarbonyl-D-alanylglicine
• 英文别名: Boc-D-Ala-Gly-OH；t-butoxycarbonyl-D-alanyl-glycine；N^α-(tert-butyloxycarbonyl)-D-alanylglycine；Boc-Ala-Gly-OH；Boc-(D)-Ala-Gly-OH；2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetic acid
• CAS: 66444-38-0
• 化学式: C₁₀H₁₈N₂O₅
• 分子量: 246.263
• InChiKey: PBGVVLQMNSPMKN-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-t-butyloxycarbonyl-D-alanylglicine 在 palladium on activated charcoal 盐酸 、 二苯基膦叠氮化物 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 155.0h， 生成 Boc-Tyr(αMe)-D-Ala-Gly-Phe-D-Leu-OH
  参考文献：
  名称：

  Novel analogs of enkephalin: identification of functional groups required for biological activity

  摘要：

  Novel tri- and tetrapeptide analogues of enkephalin, in conjunction with earlier structure-activity data, confirm that chemical substitutents present in the first and fourth residues of enkephalin are required for in vitro biological activity. A class of arylamino and alkylamino derivatized tripeptides also were found to have significant in vitro opioid-like activity indistinguishable from [D-Ala2,D-Leu5]enkephalin and morphine.

  DOI：

  10.1021/jm00184a010
• 作为产物：
  描述：

  Boc-D-Ala-Gly-OBzl 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-t-butyloxycarbonyl-D-alanylglicine
  参考文献：
  名称：

  Novel analogs of enkephalin: identification of functional groups required for biological activity

  摘要：

  Novel tri- and tetrapeptide analogues of enkephalin, in conjunction with earlier structure-activity data, confirm that chemical substitutents present in the first and fourth residues of enkephalin are required for in vitro biological activity. A class of arylamino and alkylamino derivatized tripeptides also were found to have significant in vitro opioid-like activity indistinguishable from [D-Ala2,D-Leu5]enkephalin and morphine.

  DOI：

  10.1021/jm00184a010

文献信息

• Synthesis and Properties of N.ALPHA.-(tert-Butyloxycarbonyl)peptide p-Guanidinophenyl Esters as Trypsin Substrates.
  作者：Kunihiko ITOH、Haruo SEKIZAKI、Eiko TOYOTA、Kazutaka TANIZAWA

  DOI：10.1248/cpb.43.2082

  日期：——

  Nα-(tert-Butyloxycarbonyl)peptide p-guanidinophenyl esters were synthesized by amidination of Nα-(tert-butyloxycarbonyl)peptide p-aminophenyl esters with 1-[N, N'-bis(benzyloxycarbonyl)amidino]pyrazole, followed by deprotection by catalytic hydrogenation, in good total yields. These synthetic esters were characterized as specific substrates for trypsin, and kinetic parameters for the trypsin-catalyzed hydrolysis are presented.

  Nα-(叔丁氧羰基)肽p-氨基苯酯通过Nα-(叔丁氧羰基)肽p-氨基苯酯与1-[N, N'-二(苄氧羰基)氨基]吡唑进行酰胺化合成，随后通过催化氢化去保护，获得了良好的总体产率。这些合成的酯被表征为酶胰蛋白酶的特定底物，并提供了胰蛋白酶催化水解的动力学参数。
• Pharmacologically active peptides
  申请人：Eli Lilly and Company

  公开号：US04448717A1

  公开（公告）日：1984-05-15

  Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in which R is hydrogen, methyl, ethyl, cyclopropylmethyl, or allyl; A is a residue of a D-amino acid selected from the group consisting of Ala, Abu, Nva, Val, Nle, Leu, Ile, Gly(Al), Gly(Cp), Met, Cys(Me), Met(O), Cys(Me) (O), Ser, Ser(Me), Thr, and Hse; R.sub.1 is hydrogen, C.sub.1 -C.sub.3 primary alkyl, cyclopropylmethyl, allyl, ethylthiomethyl, 2-fluoroethyl, or propargyl; X is fluoro, bromo, iodo, chloro, hydroxy, C.sub.1 -C.sub.3 alkyl, trifluoromethyl, or C.sub.1 -C.sub.2 alkoxy; and Z is methyl or ethyl; are useful analgesic agents.

  公式为##STR1##的化合物及其药学上可接受的无毒酸盐，其中R为氢，甲基，乙基，环丙甲基或烯丙基；A为从Ala，Abu，Nva，Val，Nle，Leu，Ile，Gly（Al），Gly（Cp），Met，Cys（Me），Met（O），Cys（Me）（O），Ser，Ser（Me），Thr和Hse组成的D-氨基酸残基；R.sub.1为氢，C.sub.1 -C.sub.3一级烷基，环丙甲基，烯丙基，乙硫甲基，2-氟乙基或丙炔基；X为氟，溴，碘，氯，羟基，C.sub.1 -C.sub.3烷基，三氟甲基或C.sub.1 -C.sub.2烷氧基；Z为甲基或乙基；这些化合物是有用的镇痛剂。
• Organic compounds
  申请人：Sandoz Ltd.

  公开号：US04247543A1

  公开（公告）日：1981-01-27

  The invention provides polypeptides of the formula, A-B-Gly-D-E-F wherein A is Tyr or substituted Tyr, B is, for example, -Gly-, -(D)-Ala-, or -(D)-Met-, D is Phe or substituted Phe, E is, for example, -Leu-, -Nle-, -Nva-, -Ile- or -Val-, and F is -NR.sub.7 CHR.sub.8 CH.sub.2 OR.sub.3 ', wherein, for example, R.sub.3 ' may be hydrogen or alkyl--CO--, R.sub.7 is hydrogen or alkyl and R.sub.8 is alkyl, which compounds possess pharmacological activity, for example, analgesic activity.

  本发明提供了多肽的公式A-B-Gly-D-E-F，其中A是酪氨酸或取代酪氨酸，B是例如-Gly-，-(D)-Ala-或-(D)-Met-，D是苯丙氨酸或取代苯丙氨酸，E是例如-Leu-，-Nle-，-Nva-，-Ile-或-Val-，F是-NR.sub.7 CHR.sub.8 CH.sub.2 OR.sub.3 '，其中，例如，R.sub.3'可以是氢或烷基--CO--，R.sub.7是氢或烷基，R.sub.8是烷基，这些化合物具有药理活性，例如镇痛活性。
• Selective Hydrolysis of Primary and Secondary Amides Enabled by Visible Light
  作者：Wenzhang Xiong、Yichun Wang、Xiaobo Yang、Wenbo H. Liu

  DOI：10.1021/acs.orglett.3c00354

  日期：——

  Amide hydrolysis is a fundamentally important transformation in organic chemistry. Developing hydrolysis procedures under mild conditions with a broad substrate scope is desirable. Herein, by leveraging a photoresponsive auxiliary o-nitroanilide, we established a mild two-step protocol for the hydrolysis of primary and secondary amides. This protocol is driven by visible light irradiation at room temperature

  酰胺水解是有机化学中一个根本性的重要转变。在温和条件下开发具有广泛底物范围的水解程序是可取的。在此，通过利用光响应辅助邻硝基苯胺，我们建立了一个温和的两步水解伯和仲酰胺的协议。该协议由室温下中性条件下的可见光照射驱动，可容忍许多酸和碱敏感的官能团。可以选择性地水解各种药物、天然产物和氨基酸衍生的酰胺。
• Pharmacologically active peptides, their preparation and pharmaceutical compositions containing them
  申请人：ELI LILLY AND COMPANY

  公开号：EP0030847A2

  公开（公告）日：1981-06-24

  Compounds of the formula and pharmaceutically acceptable non-toxic acid addition salts thereof, in which L and D definethe chirality; R, is hydrogen or C1-C3 primary alkyl; R2 is C1-C4 primary or secondary alkyl, allyl, cyclopropylmethyl, C1-C2 hydroxyalkyl, or -(CH2)m-U-CH3 in which U is -S- or and m is 1 or2; R3 is cyclopropylmethyl or allyl; and Z is in which R4 is hydrogen, acetyl, or acetoxymethyl and Rs is C1-C3 alkyl; are useful analgesic agents. These compounds of formula I are prepared by deblocking the correspondingly blocked tetrapeptide offormula I.

  式中的化合物 及其药学上可接受的无毒酸加成盐，其中 L 和 D 定义手性； R 是氢或 C1-C3 伯烷基； R2 是 C1-C4 伯烷基或仲烷基、烯丙基、环丙基甲基、C1-C2 羟烷基或-(CH2)m-U-CH3，其中 U 是-S-或 而 m 是 1 或 2； R3 是环丙基甲基或烯丙基；以及 Z 是 其中 R4 是氢、乙酰基或乙酰氧甲基，Rs 是 C1-C3 烷基；这些都是有用的镇痛剂。式 I 的这些化合物是通过解锁式 I 中相应的受阻四肽而制备的。